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Synthesis 2018; 50(10): 1935-1957
DOI: 10.1055/s-0036-1589532
DOI: 10.1055/s-0036-1589532
review
Recent Developments and Applications of the Chiral Brønsted Acid Catalyzed Allylboration of Carbonyl Compounds
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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For some enantioselective allylations using other allylating reagents, see:
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For a cross-metathesis/intramolecular aza-Michael process, see:
For a cross-metathesis/intramolecular Friedel–Crafts alkylation sequence, see:
The same authors have showcased the utility of other ortho-substituted benzaldehyde derivatives in DOS, see:
For some selected examples, see: