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Chiral Bronsted acid-catalyzed allylboration of aldehydes.

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.

SUBMITTER: Jain P

PROVIDER: S-EPMC2928988 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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Chiral Brønsted acid-catalyzed allylboration of aldehydes.

Jain Pankaj P Antilla Jon C JC

Journal of the American Chemical Society 20100901 34

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 croty ...[more]

PMID: 20690662

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