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Pure Appl. Chem., 1990, Vol. 62, No. 10, pp. 1993-1998

http://dx.doi.org/10.1351/pac199062101993

Stereocontrol in allylboration reactions

R. W. Hoffmann, G. Niel and A. Schlapbach

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  • Chen Jack L.-Y., Scott Helen K., Hesse Matthew J., Willis Christine L., Aggarwal Varinder K.: Highly Diastereo- and Enantioselective Allylboration of Aldehydes using α-Substituted Allyl/Crotyl Pinacol Boronic Esters via in Situ Generated Borinic Esters. J. Am. Chem. Soc. 2013, 135, 5316. <http://dx.doi.org/10.1021/ja401564z>
  • Kliman Laura T., Mlynarski Scott N., Ferris Grace E., Morken James P.: Catalytic Enantioselective 1,2-Diboration of 1,3-Dienes: Versatile Reagents for Stereoselective Allylation. Angew. Chem. 2012, 124, 536. <http://dx.doi.org/10.1002/ange.201105716>
  • Kliman Laura T., Mlynarski Scott N., Ferris Grace E., Morken James P.: Catalytic Enantioselective 1,2-Diboration of 1,3-Dienes: Versatile Reagents for Stereoselective Allylation. Angew. Chem. Int. Ed. 2012, 51, 521. <http://dx.doi.org/10.1002/anie.201105716>
  • Ito Hajime, Miya Takanori, Sawamura Masaya: Practical procedure for copper(I)-catalyzed allylic boryl substitution with stoichiometric alkoxide base. Tetrahedron 2012, 68, 3423. <http://dx.doi.org/10.1016/j.tet.2011.08.081>
  • Robinson Anna, Aggarwal Varinder K.: Stereocontrolled asymmetric synthesis of syn-E-1,4-diol-2-enes using allyl boronates and its application in the total synthesis of solandelactone F. Biomol Chem 2012, 10, 1795. <http://dx.doi.org/10.1039/c2ob06975j>
  • Hall Dennis G., Lee Jack C. H., Ding Jinyue: Catalytic enantioselective transformations of borylated substrates: Preparation and synthetic applications of chiral alkylboronates. Pure Appl. Chem. 2012, 1. <http://dx.doi.org/10.1351/PAC-CON-12-02-04>
  • Berg C. Annette, Eichenauer Nils C., Pietruszka Jörg: (2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol: Valuable reagent in the asymmetric synthesis of organoboronates. Pure Appl. Chem. 2012, 1. <http://dx.doi.org/10.1351/PAC-CON-12-03-04>
  • Kobayashi Shū, Endo Toshimitsu, Ueno Masaharu: Chiral Zinc-Catalyzed Asymmetric α-Alkylallylation and α-Chloroallylation of Aldehydes. angew chemie 2011, 123, 12470. <http://dx.doi.org/10.1002/ange.201106433>
  • Kobayashi Shū, Endo Toshimitsu, Ueno Masaharu: Chiral Zinc-Catalyzed Asymmetric α-Alkylallylation and α-Chloroallylation of Aldehydes. Angew Chem Int E 2011, 50, 12262. <http://dx.doi.org/10.1002/anie.201106433>
  • HOFFMANN R. W., NIEL G., SCHLAPBACH A.: ChemInform Abstract: Stereocontrol in Allylboration Reactions. ChemInform 2010, 22, no. <http://dx.doi.org/10.1002/chin.199105346>
  • Cho Hee Yeon, Morken James P.: Ni-Catalyzed Borylative Diene−Aldehyde Coupling: The Remarkable Effect of P(SiMe3)3. J Am Chem Soc 2010, 132, 7576. <http://dx.doi.org/10.1021/ja101513d>
  • Althaus Martin, Mahmood Adeem, Suárez José Ramón, Thomas Stephen P., Aggarwal Varinder K.: Application of the Lithiation−Borylation Reaction to the Preparation of Enantioenriched Allylic Boron Reagents and Subsequent In Situ Conversion into 1,2,4-Trisubstituted Homoallylic Alcohols with Complete Control over All Elements of Stereochemistry. J Am Chem Soc 2010, 132, 4025. <http://dx.doi.org/10.1021/ja910593w>
  • Burks Heather E., Kliman Laura T., Morken James P.: Asymmetric 1,4-Dihydroxylation of 1,3-Dienes by Catalytic Enantioselective Diboration. J Am Chem Soc 2009, 131, 9134. <http://dx.doi.org/10.1021/ja809610h>
  • Carosi Lisa, Hall Dennis G.: Chiral α-substituted allylboronates in a one-pot three-component asymmetric allylic alkylation/carbonyl allylation reaction sequence — Applications to the syntheses of (+)-(3R,5R)-3-hydroxy-5-decanolide and (–)-massoialactone. Can J Chem 2009, 87, 650. <http://dx.doi.org/10.1139/V09-036>
  • Carosi Lisa, Hall Dennis G.: Catalytic Enantioselective Preparation of α-Substituted Allylboronates: One-Pot Addition to Functionalized Aldehydes and a Route to Chiral Allylic Trifluoroborate Reagents. Angew Chem 2007, 119, 6017. <http://dx.doi.org/10.1002/ange.200700975>
  • Carosi Lisa, Hall Dennis G.: Catalytic Enantioselective Preparation of α-Substituted Allylboronates: One-Pot Addition to Functionalized Aldehydes and a Route to Chiral Allylic Trifluoroborate Reagents. Angew Chem Int Ed 2007, 46, 5913. <http://dx.doi.org/10.1002/anie.200700975>
  • Peng Feng, Hall Dennis G.: Preparation of α-substituted allylboronates by chemoselective iridium-catalyzed asymmetric allylic alkylation of 1-propenylboronates. Tetrahetron Lett 2007, 48, 3305. <http://dx.doi.org/10.1016/j.tetlet.2007.02.124>
  • Hoffmann Reinhard W., Hense Achim: Stereoselective Synthesis of Alcohols, XLIX. Tetrahydro-4-pyranols and 4-Piperidinols by Intramolecular Allylboration Reaction. Liebigs Ann /Recueil 2006, 1996, 1283. <http://dx.doi.org/10.1002/jlac.199619960807>
  • Kabalka George W., Venkataiah Bollu, Dong Gang: Baylis–Hillman chemistry: a one pot cross-coupling/allylboration reaction. Tetrahetron Lett 2005, 46, 4209. <http://dx.doi.org/10.1016/j.tetlet.2005.04.055>
  • Carosi Lisa, Lachance Hugo, Hall Dennis G.: Additions of functionalized α-substituted allylboronates to aldehydes under the novel Lewis and Brønsted acid catalyzed manifolds. Tetrahetron Lett 2005, 46, 8981. <http://dx.doi.org/10.1016/j.tetlet.2005.10.115>
  • Goldberg Steven D., Grubbs Robert H.: A One-Pot Cross-Metathesis/Allylboration Reaction: A Three-Component Coupling for the Synthesis of Functionalized Homoallylic Alcohols. Angew Chem 2002, 114, 835. <http://dx.doi.org/10.1002/1521-3757(20020301)114:5<835::AID-ANGE835>3.0.CO;2-7>
  • Ager David J., East Michael B.: The synthesis of carbohydrate derivatives from acyclic precursors. Tetrahedron 1993, 49, 5683. <http://dx.doi.org/10.1016/S0040-4020(01)87942-4>
  • Brown Herbert C., Jayaraman Seetharaman: Three-carbon ring expansion of boracyclanes. Tetrahetron Lett 1993, 34, 3997. <http://dx.doi.org/10.1016/S0040-4039(00)60599-3>
  • Tietze Lutz F., Dölle Angelika, Schiemann Kai: Diastereoselektive Addition von Allylsilanen an Aldehyde zur Synthese von enantiomerenreinen Homoallylalkoholen. Angew Chem 1992, 104, 1366. <http://dx.doi.org/10.1002/ange.19921041010>
  • Zschage Oliver, Schwark Jan-Robert, Krämer Thomas, Hoppe Dieter: Enantiomerically enriched 1-(N,N-diisopropylcarbamoyloxy)-1,3-dimethylallyllithium: stereochemistry of the stannylation, titanation, and the homoaldol reaction. Tetrahedron 1992, 48, 8377. <http://dx.doi.org/10.1016/S0040-4020(01)86586-8>
  • 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>
  • Hafner Andreas, Duthaler Rudolf O., Marti Roger, Rihs Grety, Rothe-Streit Petra, Schwarzenbach Franz: Enantioselective syntheses with titanium carbohydrate complexes. Part 7. Enantioselective allyltitanation of aldehydes with cyclopentadienyldialkoxyallyltitanium complexes. S J Am Chem Soc 1992, 114, 2321. <http://dx.doi.org/10.1021/ja00033a005>
  • Hoffmann Reinhard W., Niel Gilles: Stereoselective synthesis of alcohols, XL. Stereoselective cyclization of 7-oxo-2-heptenylboronates. Liebigs Ann Chem 1991, 1991, 1195. <http://dx.doi.org/10.1002/jlac.1991199101204>