Recent Advances in the Activation of Boron and Silicon Reagents for Stereocontrolled Allylation Reactions
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- 8 October 2003
- journal article
- review article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 42 (39) , 4732-4739
- https://doi.org/10.1002/anie.200301632
Abstract
Despite the popularity of boron and silicon allylation reagents in stereocontrolled synthesis, they suffer from a number of inherent limitations that have slowed down their development as synthetic tools for nucleophilic additions to carbonyl compounds and imine derivatives. These limitations are the low reactivity and diastereoselectivity of allyl trialkylsilane reagents, and the lack of catalytic systems for the activation and substoichiometric control of enantioselectivity in the additions of allyl boron reagents. To develop more efficient and general methods for the control of absolute stereochemistry in the resulting homoallylic alcohols, new approaches aimed at solving the problem of activation of allylic boron and silicon reagents are needed. This Minireview describes a number of recent approaches that have been devised to address this problem.Keywords
This publication has 36 references indexed in Scilit:
- A Highly Practical and Enantioselective Reagent for the Allylation of AldehydesAngewandte Chemie International Edition in English, 2003
- Strained Silacycles in Organic Synthesis: The Tandem Aldol−Allylation ReactionJournal of the American Chemical Society, 2002
- On the Mechanism of Catalytic, Enantioselective Allylation of Aldehydes with Chlorosilanes and Chiral Lewis BasesJournal of the American Chemical Society, 2000
- Transition Metal Fluoride Complexes in Asymmetric CatalysisChemistry – A European Journal, 1999
- Theoretical Study of the Effects of Structure and Substituents on Reactivity in AllylborationThe Journal of Organic Chemistry, 1998
- Enantioselective Allylation of Aldehydes Using Tartrate Ester Modified AllylsilanesChemistry Letters, 1997
- Facile and Highly Stereoselective Synthesis of Homoallylic Alcohols Using Organosilicon IntermediatesThe Journal of Organic Chemistry, 1994
- Asymmetric Allylation of Aldehydes with Chiral Lewis BasesThe Journal of Organic Chemistry, 1994
- On the stereochemistry of allylmetal‐aldehyde condensations. Preliminary communicationHelvetica Chimica Acta, 1983
- On the use of E-1-methoxymethoxybut-2-enyl(tri-n-butyl)stannane as a threo-selective, homo-enolate equivalentJournal of the Chemical Society, Chemical Communications, 1982