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Pure Appl. Chem., 1990, Vol. 62, No. 7, pp. 1209-1216

http://dx.doi.org/10.1351/pac199062071209

New enantioselective routes to biologically interesting compounds

E. J. Corey

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  • Zhu Hui, O'Leary Daniel J., Meyer Matthew P.: Stereoselection in the Corey-Bakshi-Shibata Reduction: Insight from Kinetic Isotope Effects and Transition-Structure Modeling. Angew. Chem. 2012, 124, 12060. <http://dx.doi.org/10.1002/ange.201206011>
  • Braun Manfred: The Diaryl(oxy)methyl Group: More than an Innocent Bystander in Chiral Auxiliaries, Catalysts, and Dopants. Angew Chem Int E 2012, 51, 2550. <http://dx.doi.org/10.1002/anie.201105127>
  • Zhu Hui, O'Leary Daniel J., Meyer Matthew P.: Stereoselection in the Corey-Bakshi-Shibata Reduction: Insight from Kinetic Isotope Effects and Transition-Structure Modeling. Angew. Chem. Int. Ed. 2012, 51, 11890. <http://dx.doi.org/10.1002/anie.201206011>
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  • Yıldız Tülay, Yusufoğlu Ayşe: Asymmetric synthesis of new chiral long chain alcohols. Tetrahedron: Asymmetry 2010, 21, 2981. <http://dx.doi.org/10.1016/j.tetasy.2010.12.010>
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  • Martins José E.D., Morris David J., Wills Martin: Asymmetric hydrogenation of ketones using Ir(III) complexes of N-alkyl-N’-tosyl-1,2-ethanediamine ligands. Tetrahetron Lett 2009, 50, 688. <http://dx.doi.org/10.1016/j.tetlet.2008.11.101>
  • Saavedra Jaime, Stafford Sean E., Meyer Matthew P.: Experimental transition state for the Corey–Bakshi–Shibata reduction. Tetrahetron Lett 2009, 50, 1324. <http://dx.doi.org/10.1016/j.tetlet.2009.01.033>
  • Nonappa, Maitra Uday: Unlocking the potential of bile acids in synthesis, supramolecular/materials chemistry and nanoscience. Org Biomol Chem 2008, 6, 657. <http://dx.doi.org/10.1039/b714475j>
  • Lu Gui, Kwong Fuk Yee, Ruan Ji-Wu, Li Yue-Ming, Chan Albert S. C.: Highly Enantioselective Addition of In Situ Prepared Arylzinc to Aldehydes Catalyzed by a Series of Atropisomeric Binaphthyl-Derived Amino Alcohols. Chem Eur J 2006, 12, 4115. <http://dx.doi.org/10.1002/chem.200501048>
  • Kusch Dirk, Montforts Franz-Peter: Synthesis of Enantiomerically Pure Hydroxyethylporphyrins and Their Transformation into Optically Active Chlorin Derivatives. Liebigs Ann /Recueil 2006, 1996, 83. <http://dx.doi.org/10.1002/jlac.199619960113>
  • Anwar Shaik, Periasamy Mariappan: A convenient method for the preparation of oxazaborolidine catalyst in situ using (S)-α,α-diphenylpyrrolidinemethanol, tetrabutylammonium borohydride, and methyl iodide for the asymmetric reduction of prochiral ketones. Tet Asymm 2006, 17, 3244. <http://dx.doi.org/10.1016/j.tetasy.2006.11.032>
  • Domínguez Marta, Álvarez Rosana, Borràs Emma, Farrés Jaume, Parés Xavier, de Lera Angel R.: Synthesis of enantiopure C3- and C4-hydroxyretinals and their enzymatic reduction by ADH8 from Xenopus laevis. Org Biomol Chem 2006, 4, 155. <http://dx.doi.org/10.1039/b514273c>
  • Demir Ayhan S., Sesenoglu Özge, Ülkü Dinçer, Arıcı Cengiz: Novel Enantioselective Synthesis of Both Enantiomers of Furan-2-yl Amines and Amino Acids. HCA 2003, 86, 91. <http://dx.doi.org/10.1002/hlca.200390022>
  • Kurokawa Masayuki, Shindo Takeyuki, Suzuki Masumi, Nakajima Nobuyoshi, Ishihara Kohji, Sugai Takeshi: Enzyme-catalyzed enantiomeric resolution of N-Boc-proline as the key-step in an expeditious route towards RAMP. Tet Asymm 2003, 14, 1323. <http://dx.doi.org/10.1016/S0957-4166(03)00210-6>
  • Nicolaou K. C., Snyder Scott A., Montagnon Tamsyn, Vassilikogiannakis Georgios E.: Die Diels-Alder-Reaktion in der Totalsynthese. Angew Chem 2002, 114, 1742. <http://dx.doi.org/10.1002/1521-3757(20020517)114:10<1742::AID-ANGE1742>3.0.CO;2-Y>
  • Nicolaou K. C., Snyder Scott A., Montagnon Tamsyn, Vassilikogiannakis Georgios: The Diels-Alder Reaction in Total Synthesis. Angew Chem Int Ed 2002, 41, 1668. <http://dx.doi.org/10.1002/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO;2-Z>
  • Kanth Josyula V.B., Brown Herbert C.: A new catalytic enantioselective reducing reagent system from (−)-α,α-diphenylpyrrolidinemethanol and 9-borabicyclo[3.3.1]nonane, especially effective for hindered and substituted aralkylketones. Tetrahedron 2002, 58, 1069. <http://dx.doi.org/10.1016/S0040-4020(01)01213-3>
  • Demir Ayhan S., Sesenoglu Özge, Gerçek-Arkin Zuhal: An asymmetric synthesis of both enantiomers of 2,2,2-trifluoro-1-furan-2-yl-ethylamine and 3,3,3-trifluoroalanine from 2,2,2-trifluoro-1-furan-2-yl-ethanone. Tet Asymm 2001, 12, 2309. <http://dx.doi.org/10.1016/S0957-4166(01)00410-4>
  • Arya Prabhat, Qin Huiping: Advances in Asymmetric Enolate Methodology. Tetrahedron 2000, 56, 917. <http://dx.doi.org/10.1016/S0040-4020(99)00964-3>
  • Song Yilin, Wang Quanrui, Ding Zongbiao, Tao Fenggang: Synthesis of Hydroxycedranone and Aminohydroxycedrane. Synth Common 1999, 29, 4171. <http://dx.doi.org/10.1080/00397919908085890>
  • Corey E. J., Guzman-Perez Angel: Der katalytische enantioselektive Aufbau von Molekülen mit quartären Kohlenstoff-Stereozentren. Angew Chem 1998, 110, 402. <http://dx.doi.org/10.1002/(SICI)1521-3757(19980216)110:4<402::AID-ANGE402>3.0.CO;2-6>
  • Corey Elias J., Helal Christopher J.: Reduktion von Carbonylverbindungen mit chiralen Oxazaborolidin-Katalysatoren: eine neue enantioselektive Katalyse und leistungsfähige Synthesemethode. Angew Chem 1998, 110, 2092. <http://dx.doi.org/10.1002/(SICI)1521-3757(19980803)110:15<2092::AID-ANGE2092>3.0.CO;2-M>
  • Lucet Denis, Le Gall Thierry, Mioskowski Charles: Die Chemie vicinaler Diamine. Angew Chem 1998, 110, 2724. <http://dx.doi.org/10.1002/(SICI)1521-3757(19981002)110:19<2724::AID-ANGE2724>3.0.CO;2-4>
  • González Asenslo, Granell Jaume, Pinlella Juan F., Alvarez-Larena Angel: Boron complexes of L-cysteine. Tetrahedron 1998, 54, 13313. <http://dx.doi.org/10.1016/S0040-4020(98)00816-3>
  • Dalko Peter I., Brun Virginie, Langlois Yves: A concise synthesis of (−)-mesembrine. Tetrahetron Lett 1998, 39, 8979. <http://dx.doi.org/10.1016/S0040-4039(98)02032-2>
  • Krause Norbert, Gerold Andreas: Regio- und stereoselektive Synthesen mit Organokupferreagentien. Angew Chem 1997, 109, 194. <http://dx.doi.org/10.1002/ange.19971090304>
  • Ciszewska Grazyna, Pfefferkorn Heidi, Tang Y. S., Jones Lawrence, Tarapata Richard, Sunay Ustun B.: Synthesis of tritium, deuterium, and carbon-14 labeled (S)-N-ethyl-N-methyl-3-[1-(dimethylamino)ethyl]carbamic acid, phenyl ester, (L)-2,3-dihydroxybutanedioic acid salt (SDZ ENA 713 hta), an investigational drug for the treatment of Alzheimer's Disease. J Lab Compds Radiopharm 1997, 39, 651. <http://dx.doi.org/10.1002/(SICI)1099-1344(199708)39:8<651::AID-JLCR14>3.0.CO;2-8>
  • Haiza Mohammed A., Sanyal Amitav, Snyder John K.: O-nitromandelic acid: A chiral solvating agent for the NMR determination of chiral diamine enantiomeric purity. Chirality 1997, 9, 556. <http://dx.doi.org/10.1002/(SICI)1520-636X(1997)9:5/6<556::AID-CHIR24>3.0.CO;2-M>
  • Höpfl Herbert, Farfán Norberto, Castillo Dolores, Santillan Rosa, Contreras Rosalinda, Martínez-Martínez Francisco Javier, Galván Marcelo, Alvarez Rodolfo, Fernández Lilia, Halut Sabine: Dynamic NMR and X-ray diffraction study of (N-B)-diphenyl(2-aminoethoxy) borane derivatives of ephedrines and pseudoephedrines. J Organomet Chem 1997, 544, 175. <http://dx.doi.org/10.1016/S0022-328X(97)00193-9>
  • Enders Dieter, Meiers Michaela: Diastereo- und enantioselektive Synthese von C2-symmetrischen, geschützten 1,n-Diaminen aus Dialdehyden. Angew Chem 1996, 108, 2391. <http://dx.doi.org/10.1002/ange.19961081925>
  • Vergne Fabrice, Partogyan Karolin, Aitken David J., Husson Henri-Philippe: An original synthesis of trans-1,2-diaminocyclobutane. Tetrahedron 1996, 52, 2421. <http://dx.doi.org/10.1016/0040-4020(95)01091-2>
  • Basavaiah Deevi, Dharma Rao Polisetti, Suguna Hyma Rachakonda: The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction. Tetrahedron 1996, 52, 8001. <http://dx.doi.org/10.1016/0040-4020(96)00154-8>
  • Ghosh Arun K., Mathivanan Packiarajan, Cappiello John: Conformationally constrained bis(oxazoline) derived chiral catalyst: A highly effective enantioselective Diels-Alder reaction. Tetrahetron Lett 1996, 37, 3815. <http://dx.doi.org/10.1016/0040-4039(96)00721-6>
  • Corey E.J, Helal Christopher J: Asymmetric synthesis of (S)-carbinoxamine. New aspects of oxazaborolidine-catalyzed enantioselective carbonyl reduction. Tetrahetron Lett 1996, 37, 5675. <http://dx.doi.org/10.1016/0040-4039(96)01198-7>
  • Ghosh Arun K., Mathivanan Packiarajan: Asymmetric Diels-Alder reaction: Cis-1-arylsulfonamido-2-indanols as highly effective chiral auxiliaries. Tet Asymm 1996, 7, 375. <http://dx.doi.org/10.1016/0957-4166(96)00010-9>
  • Kusch Dirk, Töllner Elke, Lincke Anngret, Montforts Franz-Peter: Eine einfache, chirogen enantioselektive Synthese von Chlorinen und Isobakteriochlorinen. Angew Chem 1995, 107, 874. <http://dx.doi.org/10.1002/ange.19951070715>
  • Quinkert Gerhard, Del Grosso Michael, Döring Astrid, Döring Wolfgang, Schenkel Ralf I., Bauch Markus, Dambacher Gernot T., Bats Jan W., Zimmermann Gottfried, Dürner Gerd: Total Synthesis with a Chirogenic Opening Move Demonstrated on Steroids with Estrane or 18a-Homoestrane Skeleton. HCA 1995, 78, 1345. <http://dx.doi.org/10.1002/hlca.19950780524>
  • Günter Aurich Hans, Gentes Christian, Harms Klaus: Enantiomerically pure 3-Oxa-2.7-diazabicyclo[3.3.0]octanes: Preparation, analysis of conformation and test for enantioselective catalysis. Tetrahedron 1995, 51, 10497. <http://dx.doi.org/10.1016/0040-4020(95)00630-Q>
  • Corey E.J., Helal Christopher J.: Novel electronic effects of remote substituents on the oxazaborolidine-catalyzed enantioselective reduction of ketones. Tetrahetron Lett 1995, 36, 9153. <http://dx.doi.org/10.1016/0040-4039(95)01961-G>
  • Kusch Dirk, Montforts Franz-Peter: Enantioselective synthesis of hematoporphyrin stereoisomers. Tet Asymm 1995, 6, 867. <http://dx.doi.org/10.1016/0957-4166(95)00091-3>
  • Kotsuki Hiyoshizo, Kuzume Hiroko, Gohda Tetsushi, Fukuhara Misako, Ochi Masamitsu, Oishi Tohru, Hirama Masahiro, Shiro Motoo: New convenient, enantiospecific synthesis of (S,S)- and (R,R)-2,2′-bipyrrolidine derivatives. Tet Asymm 1995, 6, 2227. <http://dx.doi.org/10.1016/0957-4166(95)00297-3>
  • Franot Christelle, Stone Guy B., Engeli Peter, Spöndlin Christoph, Waldvogel Erwin: A polymer-bound oxazaborolidine catalyst: Enantioselective borane reductions of ketones. Tet Asymm 1995, 6, 2755. <http://dx.doi.org/10.1016/0957-4166(95)00365-V>
  • Waldmann Herbert, Weigerding Michael, Dreisbach Claus, Wandrey Christian: C2-Symmetric Bicyclic Diols as Chiral Ligands in the titanate-catalyzed enantioselective addition of alkylzinc reagents to aldehydes. HCA 1994, 77, 2111. <http://dx.doi.org/10.1002/hlca.19940770803>
  • Periasamy Mariappan, Kanth J.V.Bhaskar, Prasad A.S.Bhanu: Convenient procedures for the asymmetric reductions utilizing α,α-diphenyl- pyrrolidinemethanol and borane complexes generated using the I2/NaBH4 system. Tetrahedron 1994, 50, 6411. <http://dx.doi.org/10.1016/S0040-4020(01)80657-8>
  • Nevalainen Vesa: Quantum chemical modeling of chiral catalysis. Part 15. On the role of hydride-bridged borane - alkoxyborane complexes in the catalytic enantioselective reduction of ketones promoted by chiral oxazaborolidines. Tet Asymm 1994, 5, 289. <http://dx.doi.org/10.1016/S0957-4166(00)86186-8>
  • Nevalainen Vesa: Quantum chemical modeling of chiral catalysis. Part 17. On the diboranc derivatives of chiral oxazaborolidines used as catalysts in the enantioselective reduction of ketones. Tet Asymm 1994, 5, 395. <http://dx.doi.org/10.1016/S0957-4166(00)86211-4>
  • Stone Guy B.: Oxazaborolidine catalyzed borane reductions of ketones: a significant effect of temperature on selectivity. Tet Asymm 1994, 5, 465. <http://dx.doi.org/10.1016/S0957-4166(00)86218-7>
  • Nevalainen Vesa: Quantum chemical modeling of chiral catalysis. Part 19. Strain and stability - oxazadiboretanes potentially involved in the enantioselective reduction of ketones promoted by chiral oxazaborolidines. Tet Asymm 1994, 5, 903. <http://dx.doi.org/10.1016/S0957-4166(00)86242-4>
  • Mulzer Johann, Dupré Susanne, Buschmann Jürgen, Luger Peter: Lineare Totalsynthese von (−)-ACRL-Toxin III B. Angew Chem 1993, 105, 1538. <http://dx.doi.org/10.1002/ange.19931051039>
  • Mulzer Johann, Dupré Susanne, Buschmann Jürgen, Luger Peter: Linear Total Synthesis of (-)-ACRL Toxin III B. Angew Chem Int Ed Engl 1993, 32, 1452. <http://dx.doi.org/10.1002/anie.199314521>
  • Klein Darryl P., Méndez N.Quirós, Seyler Jeffery W., Arif Atta M., Gladysz J.A.: Structures of propionaldehyde, butyraldehyde, and pivalaldehyde complexes of the chiral rhenium fragment [(η5-C5H5)Re(NO)(PPh3)]+. J Organomet Chem 1993, 450, 157. <http://dx.doi.org/10.1016/0022-328X(93)80152-2>
  • Nakagawa Masako, Kawate Tomohiko, Kakikawa Taro, Yamada Hideki, Matsui Teruaki, Hino Tohru: Asymmetric reductions of imines and ketones by chiral oxaborolidines. Tetrahedron 1993, 49, 1739. <http://dx.doi.org/10.1016/S0040-4020(01)80531-7>
  • Bhaskar Kanth J.V., Periasamy Mariappan: Convenient method for the synthesis of chiral α,α-diphenyl-2-pyrrolidinemethanol. Tetrahedron 1993, 49, 5127. <http://dx.doi.org/10.1016/S0040-4020(01)81877-9>
  • Bolm Carsten, Seger Andreas, Felder Marcel: Use of NaBH4/Me3SiCl in the β-hydroxysulfoximine-catalyzed enantioselective reduction of ketones. Tetrahetron Lett 1993, 34, 8079. <http://dx.doi.org/10.1016/S0040-4039(00)61455-7>
  • Bolm Carsten, Felder Marcel: β-Hydroxysulfoximines in the catalyzed enantioselective reduction of ketones with borane. Tetrahetron Lett 1993, 34, 6041. <http://dx.doi.org/10.1016/S0040-4039(00)61722-7>
  • Ma Shengming, Venanzi Lulgi M.: A versatile ruthenium catalyst for the tetrahydropyranylation of alcohols and phenols. Tetrahetron Lett 1993, 34, 5269. <http://dx.doi.org/10.1016/S0040-4039(00)73970-0>
  • Nevalainen Vesa: Quantum chemical modeling of chiral catalysis. Part 9. On the aggregation reactions of borane and chiral oxazaborolidines used as catalysts in the enantioselective reduction of ketones. Tet Asymm 1993, 4, 1505. <http://dx.doi.org/10.1016/S0957-4166(00)80352-3>
  • Nevalainen Vesa: Quantum chemical modeling of chiral catalysis. Part 10. On the complexes of carbonyl compounds with chiral N-sulfonylated 1,3,2-oxazaborolidines used as catalysts in the enantioselective diels-alder reactions. Tet Asymm 1993, 4, 1565. <http://dx.doi.org/10.1016/S0957-4166(00)80360-2>
  • Nevalainen Vesa: Quantum chemical modeling of chiral catalysis. Part 11. Isomerism in borane adducts of chiral oxazaborolidines used as catalysts in the enantioselective reduction of ketones ?. Tet Asymm 1993, 4, 1569. <http://dx.doi.org/10.1016/S0957-4166(00)80361-4>
  • Nevalainen Vesa: Quantum chemical modeling of chiral catalysis. Part 12. On the influence of the nature of the ring system on binding in ketone - borane complexes of chiral oxazaborolidines used as catalysts in the enantioselective reduction of ketones. Tet Asymm 1993, 4, 1597. <http://dx.doi.org/10.1016/S0957-4166(00)80365-1>
  • Nevalainen Vesa: Quantum chemical modeling of chiral catalysis. Part 14. On the coordination of carbonyl compounds to diaza-, oxaza- and dioxaluminolidines of potential use as chiral controllers in organic synthetic chemistry. Tet Asymm 1993, 4, 2517. <http://dx.doi.org/10.1016/S0957-4166(00)82232-6>
  • Dauelsberg Ch., Martens J.: Enantioselective Catalytic Borane Reductions of Achiral Ketones: Synthesis and Application of New Rigid Catalysts Prepared from (R)-Phenylglycine and (S)-Phenylalanine. Synth Common 1993, 23, 2091. <http://dx.doi.org/10.1080/00397919308018602>
  • Lohray Braj B., Bhushan Vidya: Oxazaborolidine und Dioxaborolidine in der enantioselektiven Katalyse0. Angew Chem 1992, 104, 740. <http://dx.doi.org/10.1002/ange.19921040607>
  • Stará Irena G., Starý Ivo, Závada Jiří: Optically pure (S)- and (R)-4,5-dihydro-3H-4-methyldinaphth[2,1-c; 1′,2′-e]azepines. Application to the synthesis of new bidentate ligands with axial asymmetry. Tet Asymm 1992, 3, 1365. <http://dx.doi.org/10.1016/0957-4166(92)80007-J>
  • Nevalainen Vesa: Quantum chemical modeling of chiral catalysis. Part 7. On the effects controlling the coordination of borane to chiral oxazaborolidines used as catalysts in the enantioselective reduction of ketones. Tet Asymm 1992, 3, 1441. <http://dx.doi.org/10.1016/0957-4166(92)80021-N>
  • Kanemasa Shuji, Onimura Kenjiro: New chiral auxiliaries based on conformation control, a C2-symmetric 2,2-dimethylimidazolidine and 4-chiral, 2,2-dialkyloxazolidines. Synthesis and conformational analysis of acrylamide derivatives. Tetrahedron 1992, 48, 8631. <http://dx.doi.org/10.1016/S0040-4020(01)89439-4>
  • Ager David J., East Michael B.: Methodology to establish 1,2- and 1,3-difunctionality for the synthesis of carbohydrate derivates. Tetrahedron 1992, 48, 2803. <http://dx.doi.org/10.1016/S0040-4020(01)90970-6>
  • Corey E.J., Link John O., Sarshar Sepehr, Shao Yang: X-ray diffraction studies of crystalline trihalomethyl ketones (RCOCX3) reveal an unusual structural deformation about the carbonyl group. Tetrahetron Lett 1992, 33, 7103. <http://dx.doi.org/10.1016/S0040-4039(00)60847-X>
  • Corey E.J., Link John O., Bakshi Raman K.: A mechanistic and structural analysis of the basis for high enantioselectivity in the oxazaborolidine-catalyzed reduction of trihalomethyl ketones by catecholborane. Tetrahetron Lett 1992, 33, 7107. <http://dx.doi.org/10.1016/S0040-4039(00)60848-1>
  • Corey E.J., Yi Kyu Yang, Matsuda Seiichi P.T.: Catalytic enatioselective synthesis of (3S)-2,3-oxidosqualene. Tetrahetron Lett 1992, 33, 2319. <http://dx.doi.org/10.1016/S0040-4039(00)74200-6>
  • Corey E.J., Cimprich Karlene A.: Enantioselective routes to chiral benzylic thiols, sulfinic esters and sulfonic acids illustrated by the 1-phenylethyl series. Tetrahetron Lett 1992, 33, 4099. <http://dx.doi.org/10.1016/S0040-4039(00)74662-4>
  • Corey E.J., Link John O.: A new process for the generation of 1,3,2-oxazaborolidines, catalysts for enantioselective synthesis. Tetrahetron Lett 1992, 33, 4141. <http://dx.doi.org/10.1016/S0040-4039(00)74673-9>
  • Corey E.J., Azimioara Mihai, Sarshar Sepehr: X-Ray crystal structure of a chiral oxazaborolidine catalyst for enantioselective carbonyl reduction. Tetrahetron Lett 1992, 33, 3429. <http://dx.doi.org/10.1016/S0040-4039(00)92654-6>
  • Corey E.J., Link John O.: A new process for the enantioselective synthesis of chiral α-aryloxy- and α-hydroxy acids. Tetrahetron Lett 1992, 33, 3431. <http://dx.doi.org/10.1016/S0040-4039(00)92655-8>
  • Corey E.J., Link John O., Shao Yang: Two effective procedures for the synthesis of trichloromethyl ketones, useful precursors of chiral α-amino and α-hydroxy acids. Tetrahetron Lett 1992, 33, 3435. <http://dx.doi.org/10.1016/S0040-4039(00)92656-X>
  • Rao A.V.Rama, Gurjar M.K., Kaiwar Vijay: Enantioselective catalytic reductions of ketones with new four membered oxazaborolidines: Application to (S)-tetramisole. Tet Asymm 1992, 3, 859. <http://dx.doi.org/10.1016/S0957-4166(00)82184-9>
  • Nevalainen Vesa: Quantum chemical modeling of chiral catalysis. Part 5. On the role of alkoxyboranes in the catalytic enantioselective reduction of carbonyl compounds by the CBS method. Tet Asymm 1992, 3, 921. <http://dx.doi.org/10.1016/S0957-4166(00)82190-4>
  • Nevalainen Vesa: Quantum chemical modeling of chiral catalysis. Part 6. On the relative stability of dimers of chiral oxazaborolidines used in the catalytic enantioselective reduction of ketones. Tet Asymm 1992, 3, 933. <http://dx.doi.org/10.1016/S0957-4166(00)82191-6>
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