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. 2010 Sep 1;132(34):11884-6.
doi: 10.1021/ja104956s.

Chiral Brønsted acid-catalyzed allylboration of aldehydes

Pankaj Jain  1 , Jon C Antilla
Affiliations

Chiral Brønsted acid-catalyzed allylboration of aldehydes

Pankaj Jain et al. J Am Chem Soc. .

Abstract

The catalytic enantioselective allylation of aldehydes is a long-standing problem of considerable interest to the chemical community. We disclose a new high-yielding and highly enantioselective chiral Brønsted acid-catalyzed allylboration of aldehydes. The reaction is shown to be highly general, with a broad substrate scope that covers aryl, heteroaryl, alpha,beta-unsaturated, and aliphatic aldehydes. The reaction conditions are also shown to be effective for the catalytic enantioselective crotylation of aldehydes. We believe that the high reactivity of the allylboronate is due to protonation of the boronate oxygen by the chiral phosphoric acid catalyst.

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Figures

Figure 1
Figure 1
A plausible transition state assembly for chiral phosphoric-acid allylation of aldehydes.
See this image and copyright information in PMC

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