Synthesis 2018; 50(10): 1935-1957
DOI: 10.1055/s-0036-1589532
review
© Georg Thieme Verlag Stuttgart · New York

Recent Developments and Applications of the Chiral Brønsted Acid Catalyzed Allylboration of Carbonyl Compounds

Daniel M. Sedgwick
a  Departamento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain   Email: pablo.barrio@uv.es
b  Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia, Spain
,
Matthew N. Grayson
c  Centre for Molecular Informatics, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK
,
Santos Fustero
a  Departamento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain   Email: pablo.barrio@uv.es
b  Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia, Spain
,
Pablo Barrio*
a  Departamento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain   Email: pablo.barrio@uv.es
› Author Affiliations
We thank the Spanish MINECO (CTQ2013-43310 and CTQ2017-84249-P) 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.
Further Information

Publication History

Received: 04 December 2017

Accepted after revision: 16 January 2018

Publication Date:
11 April 2018 (online)


In memory of Prof José Barluenga

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% ee 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.

1 Introduction

2 Early Developments

3 Synthetic Applications

4 Variants

5 Computational Contribution

6 Conclusions

 
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