Issue 38, 2018

Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides

Abstract

γ,δ-Unsaturated amides in which the alkene moiety bears an aryl or heteroaryl substituent undergo regioselective rhodium-catalyzed δ-borylation by pinacolborane to afford chiral secondary benzylic boronic esters. The results contrast the γ-borylation of γ,δ-unsaturated amides in which the disubstituted alkene moiety bears only alkyl substituents; the reversal in regiochemistry is coupled with a reversal in the sense of π-facial selectivity.

Graphical abstract: Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides

Supplementary files

Article information

Article type
Communication
Submitted
26 Feb 2018
Accepted
17 Apr 2018
First published
20 Apr 2018

Chem. Commun., 2018,54, 4838-4841

Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides

G. L. Hoang, S. Zhang and J. M. Takacs, Chem. Commun., 2018, 54, 4838 DOI: 10.1039/C8CC01563E

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