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Recent developments and applications of the chiral Brønsted acid catalyzed allylboration of carbonyl compounds

Accepted version
Peer-reviewed

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Type

Article

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Authors

Sedgwick, Daniel M 
Grayson, MN 
Fustero, Santos 
Barrio, Pablo 

Abstract

The 50-year-old allylboration reaction has seen dramatic developments since the dawn of the new century after the first catalytic asymmetric versions came into play. In the past decade alone, several methodologies capable of achieving the desired homoallylic alcohols in over 90% e.e. have been developed. This review focuses on the chiral Brønsted acid-catalyzed allylboration reaction—covering everything from the very first examples and precedents to modern day variations and applications—and includes the following sections:

  1. Introduction
  2. Early developments
  3. Synthetic applications
  4. Variants
  5. Computational contribution

Description

Keywords

asymmetric synthesis, allylboration, enantioselective catalysis­, chiral Brønsted acids, homoallylic alcohols, DFT calculations

Journal Title

Synthesis

Conference Name

Journal ISSN

0039-7881
1437-210X

Volume Title

50

Publisher

Thieme
Sponsorship
We thank the Spanish MINECO (CTQ2013-43310) and Generalitat Valenciana (PROMETEOII/2014/073) for their financial support. D. M. S. is grateful to the Spanish Government for an FPU fellowship. We are grateful to Girton College, Cambridge (Research Fellowship to M.N.G.) for financial support.