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

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

Key words

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

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