Pure Appl. Chem., 1988, Vol. 60, No. 11, pp. 1597-1606
http://dx.doi.org/10.1351/pac198860111597
Enantioselective alkylation of carbonyl compounds. From stoichiometric to catalytic asymmetric induction
CrossRef Cited-by Linking
- Dong Junyu, Li Tianbin, Dai Chuan, Weng Wen, Xue Xinghua, Zhang Yuyu, Zeng Qingle: Protecting-group-free palladium-catalyzed hydroxylation, C-O and C-N coupling of chiral 6-bromo- and 6,6’-dibromo- 1,1’-binaphthols. Appl. Organometal. Chem. 2013, 27, 337. <http://dx.doi.org/10.1002/aoc.2982>
- Harrison-Marchand Anne, Mongin Florence: Mixed AggregAte (MAA): A Single Concept for All Dipolar Organometallic Aggregates. 1. Structural Data. Chem. Rev. 2013, 113, 7470. <http://dx.doi.org/10.1021/cr300295w>
- Mongin Florence, Harrison-Marchand Anne: Mixed AggregAte (MAA): A Single Concept for All Dipolar Organometallic Aggregates. 2. Syntheses and Reactivities of Homo/HeteroMAAs. Chem. Rev. 2013, 113, 7563. <http://dx.doi.org/10.1021/cr3002966>
- Lichtenberg Crispin, Spaniol Thomas P., Peckermann Ilja, Hanusa Timothy P., Okuda Jun: Cationic, Neutral, and Anionic Allyl Magnesium Compounds: Unprecedented Ligand Conformations and Reactivity Toward Unsaturated Hydrocarbons. J. Am. Chem. Soc. 2013, 135, 811. <http://dx.doi.org/10.1021/ja310112e>
- Chevallier Floris, Mongin Florence, Gros Philippe C., Catel Delphine: Chiral Organomagnesiates as Dual Reagents for Bromine-Magnesium Exchange of 2-Bromopyridine and Access to Chiral α-Substituted 2-Pyridylcarbinols. Eur J Org 2012, 2012, 53. <http://dx.doi.org/10.1002/ejoc.201101490>
- Catel Delphine, Payen Olivier, Chevallier Floris, Mongin Florence, Gros Philippe C.: Pyridylmagnesiates: generation by bromine–metal exchange and enantioselective addition to aldehydes. Tetrahedron 2012, 68, 4018. <http://dx.doi.org/10.1016/j.tet.2012.03.058>
- Payen Olivier, Chevallier Floris, Mongin Florence, Gros Philippe C.: Straightforward access to enantioenriched pyrazyl alcohols using chiral organomagnesiates. Tetrahedron: Asymmetry 2012, 23, 1678. <http://dx.doi.org/10.1016/j.tetasy.2012.11.003>
- Zong Hua, Huang Huayin, Liu Junfeng, Bian Guangling, Song Ling: Added-Metal-Free Catalytic Nucleophilic Addition of Grignard Reagents to Ketones. J Org Chern 2012, 77, 4645. <http://dx.doi.org/10.1021/jo3004277>
- Chinkov Nicka, Warm Aleksander, Carreira Erick M.: Eine verbesserte Synthese von Efavirenz durch asymmetrische Autokatalyse. Angew Chem 2011, 123, 3014. <http://dx.doi.org/10.1002/ange.201006689>
- Chinkov Nicka, Warm Aleksander, Carreira Erick M.: Asymmetric Autocatalysis Enables an Improved Synthesis of Efavirenz. Angew Chem Int Ed 2011, 50, 2957. <http://dx.doi.org/10.1002/anie.201006689>
- Liu Chang-Lu, Wei Chang-Yong, Wang Shi-Wen, Peng Yun-Gui: A systematic study of chiral homoprolinols and their derivatives in the catalysis of enantioselective addition of diethylzinc to aldehydes. Chirality 2011, 23, 921. <http://dx.doi.org/10.1002/chir.21017>
- Sun Yin-Wei, Jiang Jia-Jun, Zhao Mei-Xin, Wang Fei-Jun, Shi Min: Palladium-catalyzed asymmetric allylic substitutions in the presence of chiral phosphine-imine type ligands. J Organomet Chem 2011, 696, 2850. <http://dx.doi.org/10.1016/j.jorganchem.2011.04.036>
- Eidamshaus Christian, Reissig Hans-Ulrich: Application of novel enantiopure hydroxymethyl-substituted pyridine derivatives in asymmetric catalysis. Tet Asymm 2011, 22, 1644. <http://dx.doi.org/10.1016/j.tetasy.2011.08.017>
- Jagtap R.S., Joshi N.N.: Bidentate ligand-catalyzed enantioselective addition of RZnX to benzaldehyde. Tetrahedron Letters 2011, 52, 6501. <http://dx.doi.org/10.1016/j.tetlet.2011.09.120>
- Lin Li, Zhang Jinlong, Ma Xiaojuan, Fu Xu, Wang Rui: Bifunctional 3,3′-Ph2-BINOL-Mg Catalyzed Direct Asymmetric Vinylogous Michael Addition of α,β-Unsaturated γ-Butyrolactam. Org Lett 2011, 13, 6410. <http://dx.doi.org/10.1021/ol202713f>
- Mei Liang-yong, Yuan Zhi-liang, Shi Min: Chiral Imidazoline–Phosphine Ligands for Palladium-Catalyzed Asymmetric Allylic Substitutions. Organomettalics 2011, 30, 6466. <http://dx.doi.org/10.1021/om2008309>
- Chang-Tao Qian, Tai-Sheng Huang: Enantioselective allylation of aldehydes with chiral allyl organolanthanide reagents. Chin J Chem 2010, 16, 272. <http://dx.doi.org/10.1002/cjoc.19980160312>
- Shi Min, Duan Wei-Liang, Rong Guo-Bin: Axially Dissymmetric Chiral (R)-N, W-Bis(2-hydroxy-3,5-ditert-butyl-arylmethyl)-1, 1′-binaphthalene-2,2′-diamine as Chiral Ligands in the Reaction of Diethylzinc to Aldehydes†. Chin J Chem 2010, 20, 1319. <http://dx.doi.org/10.1002/cjoc.20020201127>
- Bao Hongli, Wu Jiang, Li Hongji, Wang Zheng, You Tianpa, Ding Kuiling: Enantioselective Ring Opening Reaction of meso-Epoxides with Aromatic and Aliphatic Amines Catalyzed by Magnesium Complexes of BINOL Derivatives. Eur J Org Chem 2010, 2010, 6722. <http://dx.doi.org/10.1002/ejoc.201001222>
- Dreher Marian A., Krumm Michael, Lizandara-Pueyo Carlos, Polarz Sebastian: Chromium containing zinc oxide materials from organobimetallic precursors. Dalton Trans 2010, 39, 2232. <http://dx.doi.org/10.1039/b916253b>
- Bailey William F., Luderer Mark R., Fair Justin D., Dancer Robert J., Sommer Michael Bech, Luderer Matthew R.: Asymmetric addition of achiral organomagnesium reagents or organolithiums to achiral aldehydes or ketones: a review. Tet Asymm 2009, 20, 981. <http://dx.doi.org/10.1016/j.tetasy.2009.03.015>
- Pavlov Valeri A.: C2 and C1 Symmetry of chiral auxiliaries in catalytic reactions on metal complexes. Tetrahedron 2008, 64, 1147. <http://dx.doi.org/10.1016/j.tet.2007.10.078>
- Pisani Laura, Superchi Stefano: 1,1′-Binaphthylazepine-based ligands for the enantioselective dialkylzinc addition to aromatic aldehydes. Tet Asymm 2008, 19, 1784. <http://dx.doi.org/10.1016/j.tetasy.2008.07.026>
- Qin Ying-Chuan, Pu Lin: Highly Enantioselective Addition of Diphenylzinc to Aliphatic and Aromatic Aldehydes Catalyzed by a Readily Available H8-Binol Derivative. Angew Chem 2006, 118, 279. <http://dx.doi.org/10.1002/ange.200503206>
- Qin Ying-Chuan, Pu Lin: Highly Enantioselective Addition of Diphenylzinc to Aliphatic and Aromatic Aldehydes Catalyzed by a Readily Available H8-Binol Derivative. Angew Chem Int Ed 2006, 45, 273. <http://dx.doi.org/10.1002/anie.200503206>
- Arnott Gareth, Hunter Roger: Enantioselective addition of diethylzinc to benzaldehyde catalysed by chiral, bridged resorcinarenes: a stereoselectivity model based on chirality transfer. Tetrahedron 2006, 62, 992. <http://dx.doi.org/10.1016/j.tet.2005.10.030>
- Mamula Olimpia, von Zelewsky Alex, Brodard Pierre, Schläpfer Carl-Wilhelm, Bernardinelli Gérald, Stoeckli-Evans Helen: Helicates of Chiragen-Type Ligands and Their Aptitude for Chiral Self-Recognition. Chem Eur J 2005, 11, 3049. <http://dx.doi.org/10.1002/chem.200401109>
- Arnott Gareth, Heaney Harry, Hunter Roger, Page Philip C. B.: Synthesis of the First Chiral, Functionalised-Bridged Resorcinarenes in Asymmetric Catalysis: Evidence for Intracavity Asymmetric Catalysis. Eur J Org Chem 2004, 2004, 5126. <http://dx.doi.org/10.1002/ejoc.200400615>
- Matsunaga Nobuyuki, Kaku Tomohiro, Ojida Akio, Tasaka Akihiro: Synthetic studies on (1S)-1-(6,7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl)-2-methylpropan-1-ol as a selective C17,20-lyase inhibitor. Tet Asymm 2004, 15, 2021. <http://dx.doi.org/10.1016/j.tetasy.2004.05.044>
- Zhang Wen, Xu Qin, Shi Min: Palladium-catalyzed asymmetric allylic substitutions by axially chiral P,S-, S,S-, and S,O-heterodonor ligands with a binaphthalene framework. Tet Asymm 2004, 15, 3161. <http://dx.doi.org/10.1016/j.tetasy.2004.08.008>
- Tseng Shi-Liang, Yang Teng-Kuei: The application of chiral amino thiols as catalysts in the enantioselective addition of diethylzinc to aldehydes. Tet Asymm 2004, 15, 3375. <http://dx.doi.org/10.1016/j.tetasy.2004.08.009>
- Zhang Wen, Shi Min: Axially chiral P,S-heterodonor ligands with a binaphthalene framework for palladium-catalyzed asymmetric allylic substitutions: experimental investigation on the reversal of enantioselectivity between different alkyl groups on sulfur atom. Tet Asymm 2004, 15, 3467. <http://dx.doi.org/10.1016/j.tetasy.2004.09.027>
- Shi Min, Wang Chun-Jiang: Axially dissymmetric (R)-(+)-5,5′,6,6′,7,7′,8,8′ octahydro-[1,1′]binaphthyldiimine chiral salen type-ligands for copper-catalyzed asymmetric aziridination. Chirality 2002, 14, 412. <http://dx.doi.org/10.1002/chir.10107>
- Henderson Kenneth W, Kerr William J, Moir Jennifer H: Magnesium amide base-mediated enantioselective deprotonation processes. Tetrahedron 2002, 58, 4573. <http://dx.doi.org/10.1016/S0040-4020(02)00364-2>
- Shaikh Nadim S, Deshpande Vishnu H, Bedekar Ashutosh V: New polymer anchored chiral amino oxazolines as effective catalysts for enantioselective addition of diethylzinc to aldehydes. Tetrahetron Lett 2002, 43, 5587. <http://dx.doi.org/10.1016/S0040-4039(02)01139-5>
- Shi Min, Wang Chun-Jiang: Axially dissymmetric binaphthyldiimine chiral Salen-type ligands for catalytic asymmetric addition of diethylzinc to aldehyde. Tet Asymm 2002, 13, 2161. <http://dx.doi.org/10.1016/S0957-4166(02)00571-2>
- Noyori Ryoji, Suga Seiji, Oka Hiromasa, Kitamura Masato: Self and nonself recognition of chiral catalysts: The origin of nonlinear effects in the amino-alcohol catalyzed asymmetric addition of diorganozincs to aldehydes. Chem Record 2001, 1, 85. <http://dx.doi.org/10.1002/tcr.1>
- Panev Stefan, Linden Anthony, Dimitrov Vladimir: Chiral aminoalcohols with a menthane skeleton as catalysts for the enantioselective addition of diethylzinc to benzaldehyde. Tet Asymm 2001, 12, 1313. <http://dx.doi.org/10.1016/S0957-4166(01)00206-3>
- Dimitrov Vladimir, Dobrikov Georgi, Genov Miroslav: Chiral β- and γ-aminoalcohols derived from (+)-camphor and (−)-fenchone as catalysts for the enantioselective addition of diethylzinc to benzaldehyde. Tet Asymm 2001, 12, 1323. <http://dx.doi.org/10.1016/S0957-4166(01)00221-X>
- Shi Min, Wang Chuan-Jiang, Chan Albert S.C.: Axially dissymmetric binaphthyldiimine chiral salen-type ligands for copper-catalyzed asymmetric aziridination. Tet Asymm 2001, 12, 3105. <http://dx.doi.org/10.1016/S0957-4166(01)00534-1>
- Shi Min, Sui Wen-Sheng: Trifluoromethanesulfonamide, diphenylphosphoramide and diphenylthiophosphoramide of (R)-(+)-1,1′-binaphthyl-2,2′-diamine as chiral catalyst ligands for the titanium(IV) alkoxide-promoted addition of diethylzinc to aldehydes. Chirality 2000, 12, 574. <http://dx.doi.org/10.1002/1520-636X(2000)12:7<574::AID-CHIR5>3.0.CO;2-S>
- Bolm Carsten, Hermanns Nina, Hildebrand Jens P., Muñiz Kilian: Asymmetric, Catalytic Phenyl Transfer to Aldehydes: Enantioselective Synthesis of Diarylmethanols. Angew Chem 2000, 112, 3607. <http://dx.doi.org/10.1002/1521-3757(20001002)112:19<3607::AID-ANGE3607>3.0.CO;2-A>
- Bolm Carsten, Hermanns Nina, Hildebrand Jens P., Muñiz Kilian: Asymmetric, Catalytic Phenyl Transfer to Aldehydes: Enantioselective Synthesis of Diarylmethanols. Angew Chem 2000, 39, 3465. <http://dx.doi.org/10.1002/1521-3773(20001002)39:19<3465::AID-ANIE3465>3.0.CO;2-4>
- Kitamura Masato, Oka Hiromasa, Noyori Ryoji: Asymmetric addition of dialkylzincs to benzaldehyde derivatives catalyzed by chiral β-amino alcohols. Evidence for the monomeric alkylzinc aminoalkoxide as catalyst. Tetrahedron 1999, 55, 3605. <http://dx.doi.org/10.1016/S0040-4020(98)01167-3>
- Knochel Paul, Almena Perea Juan J., Jones Philip: Organozinc mediated reactions. Tetrahedron 1998, 54, 8275. <http://dx.doi.org/10.1016/S0040-4020(98)00318-4>
- Hoppe Dieter, Hense Thomas: Enantioselektive Synthese mit Lithium/(−)-Spartein-Carbanion-Paaren. Angew Chem 1997, 109, 2376. <http://dx.doi.org/10.1002/ange.19971092105>
- Cheng Guo, Jun Qiu, Zhang Xumu, Verdugo Dawn, Larter Martin L., Christie Ray, Kenney Patrick, Walsh Patrick J.: Enantioselective addition of diethylzinc to benzaldehyde catalyzed by chiral titanate complexes with helical ligands. Tetrahedron 1997, 53, 4145. <http://dx.doi.org/10.1016/S0040-4020(97)00134-8>
- Genov Miroslav, Kostova Kalina, Dimitrov Vladimir: Highly diastereoselective synthesis of new optically active aminoalcohols in one step from (+)-camphor and (−)-fenchone. Tet Asymm 1997, 8, 1869. <http://dx.doi.org/10.1016/S0957-4166(97)00182-1>
- Genov Miroslav, Dimitrov Vladimir, Ivanova Valentina: New δ-aminoalcohol for the enantioselective addition of dialkylzincs to aldehydes. Tet Asymm 1997, 8, 3703. <http://dx.doi.org/10.1016/S0957-4166(97)00534-X>
- Kitamura Masato, Yamakawa Masashi, Oka Hiromasa, Suga Seiji, Noyori Ryoji: Homochiral and Heterochiral Dimers of the Methylzinc Alkoxide Formed from Dimethylzinc and Enantiomeric 3-exo-(Dimethylamino)isoborneol—Origin of the Distinct Differences in Solution-Phase Behavior and Crystal Structures. Chem Eur J 1996, 2, 1173. <http://dx.doi.org/10.1002/chem.19960020921>
- Dimitrov Vladimir, Simova Svetlana, Kostova Kalina: Highly effective and practical stereoselective synthesis of new homoallylic alcohols with (+)-camphor and (−)-fenchone skeleton. Tetrahedron 1996, 52, 1699. <http://dx.doi.org/10.1016/0040-4020(95)01005-X>
- Greeves Nicholas, Pease J.Elizabeth: Enantioselective addition of tris(TADDOL) organocerium reagents to aldehydes. Tetrahetron Lett 1996, 37, 5821. <http://dx.doi.org/10.1016/0040-4039(96)01236-1>
- Maciejewski Lucien A., Goetgheluck Sophie J., Delacroix Olivier A., Brocard Jacques S.: Highly stereoselective alkylation through asymmetric intramolecular autoactivation; synthesis and use of a new chiral ligand. Tet Asymm 1996, 7, 1573. <http://dx.doi.org/10.1016/0957-4166(96)00184-X>
- Dimitrov Vladimir, Genov Miroslav, Simova Svetlana, Linden Anthony: Cerium(III) chloride mediated addition of mono- and dilithium ferrocene to (+)-camphor and (−)-fenchone: synthesis and structure of new chiral ferrocenyl alcohols and diols. J Organomet Chem 1996, 525, 213. <http://dx.doi.org/10.1016/S0022-328X(96)06498-4>
- Berrisford David J., Bolm Carsten, Sharpless K. Barry: Ligandenbeschleunigte Katalyse. Angew Chem 1995, 107, 1159. <http://dx.doi.org/10.1002/ange.19951071004>
- Knochel Paul, Vettel Stephan, Eisenberg Christina: Catalytic asymmetric synthesis of chiral secondary polyfunctional alcohols using diorganozincs. Appl Organometal Chem 1995, 9, 175. <http://dx.doi.org/10.1002/aoc.590090303>
- Togni Antonio, Venanzi Luigi M.: Stickstoffdonoren in der Organometallchemie und in der Homogenkatalyse. Angew Chem 1994, 106, 517. <http://dx.doi.org/10.1002/ange.19941060504>
- Khristoforov V. L., Serebryanyi V. A.: Methods for obtaining optically active intermediates for prostaglandin synthesis [review]. Pharm Chem J 1994, 28, 412. <http://dx.doi.org/10.1007/BF02285402>
- Markó Istvan E, Chesney Antony, Hollinshead David M: Asymmetric grignard addition to aldéhydes. An example of inverse temperature dependence of enantiomeric excess. Tet Asymm 1994, 5, 569. <http://dx.doi.org/10.1016/0957-4166(94)80020-0>
- Nicolosi Giovanni, Patti Angela, Morrone Raffaele, Piattelli Mario: Enantiopure 1-hydroxymethyl-2-dimethylaminomethylferrocene as efficient catalyst in the enantioselective addition of diethylzinc to aldehydes. Tet Asymm 1994, 5, 1639. <http://dx.doi.org/10.1016/0957-4166(94)80069-3>
- Noyori Ryoji: Organometallic ways for the multiplication of chirality. Tetrahedron 1994, 50, 4259. <http://dx.doi.org/10.1016/S0040-4020(01)89365-0>
- Bolm Carsten, Müller Jürgen: Spectroscopic studies on the β-hydroxysulfoximine-catalyzed enantioselective alkylation of aldehydes. Tetrahedron 1994, 50, 4355. <http://dx.doi.org/10.1016/S0040-4020(01)89372-8>
- Weber Beat, Seebach Dieter: Highly enantioselective addition of primary alkyl Grignard reagents to carbocyclic and heterocyclic arylketones in the presence of magnesium TADDOLate preparative and mechanistic aspects. Tetrahedron 1994, 50, 6117. <http://dx.doi.org/10.1016/S0040-4020(01)90463-6>
- Brieden Walter, Ostwald Roswitha, Knochel Paul: Enantioselektive katalytische Addition funktionalisierter Dialkylzinkverbindungen an β-stannylierte Aldehyde; eine einfache Methode zur Herstellung nichtracemischer β- und γ-funktionalisierter sekundärer Alkohole. Angew Chem 1993, 105, 629. <http://dx.doi.org/10.1002/ange.19931050438>
- Motevalli Majid, O'Brien Paul, Robinson Andrew J., Walsh John R., Wyatt Peter B., Jones A.C.: The preparation, reactivity, and crystal structure of a 1 : 1 adduct of dimethylzinc and (−)-sparteine. J Organomet Chem 1993, 461, 5. <http://dx.doi.org/10.1016/0022-328X(93)83264-V>
- Carreño M.Carmen, García Ruano José L., Maestro M.Carmen, Martín Cabrejas Luisa M.: Catalytic activity of chiral β-hydroxysulfoxides in the enantioselective addition of diethylzinc to benzaldehyde. Tet Asymm 1993, 4, 727. <http://dx.doi.org/10.1016/S0957-4166(00)80181-0>
- Chibale Kelly, Greeves Nicholas, Lyford Lisa, Pease J.Elizabeth: New homochiral binaphthol-modified organolanthanide reagents for the enantioselective addition to aldehydes. Tet Asymm 1993, 4, 2407. <http://dx.doi.org/10.1016/S0957-4166(00)82211-9>
- Wally Hans, Widhalm Michael, Weissensteiner Walter, Schlögl Karl: A homoannularly bridged hydroxyamino ferrocene as an efficient catalyst for the enantioselective ethylation of aromatic and aliphatic aldehydes. Tet Asymm 1993, 4, 285. <http://dx.doi.org/10.1016/S0957-4166(00)86069-3>
- Dietz Steven D., Eilerts Nancy W., Heppert Joseph A.: Präzedenzloser stereospezifischer Ligandenaustausch an einem WW-Templat. Angew Chem 1992, 104, 67. <http://dx.doi.org/10.1002/ange.19921040117>
- Bolm Carsten, Schlingloff Gunther, Harms Klaus: Catalyzed Enantioselective Alkylation of Aldehydes. Chem Ber 1992, 125, 1191. <http://dx.doi.org/10.1002/cber.19921250529>
- 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>
- Noyori Ryoji, Kitamura Masato: Enantioselektive Addition von Organometallreagentien an Carbonylverbindungen: Übertragung, Vervielfältigung und Verstärkung der Chiralität. Angew Chem 1991, 103, 34. <http://dx.doi.org/10.1002/ange.19911030106>
- Rosini Carlo, Franzini Livia, Iuliano Anna, Pini Dario, Salvadori Piero: Asymmetric alkylation of aromatic aldehydes by diethyl zinc in the presence of (S)-N,N,N′,N′,-tetramethyl-2,2′-diamino-1,1′-binaphthyl. Tet Asymm 1991, 2, 363. <http://dx.doi.org/10.1016/S0957-4166(00)82120-5>
- Noyori R., Suga S., Kawai K., Okada S., Kitamura M., Oguni N., Hayashi M., Kaneko T., Matsuda Y.: Enantioselective addition of diorganozincs to aldehydes catalyzed by β-amino alcohols. J Organomet Chem 1990, 382, 19. <http://dx.doi.org/10.1016/0022-328X(90)85212-H>