Issue 18, 2010

Stereoselective synthesis of vinyl-substituted (Z)-stilbenes by rhodium-catalysed addition of arylboronic acids to allenic alcohols

Abstract

Vinyl-substituted (Z)-stilbenes are stereoselectively synthesised on treatment of 4-arylbuta-2,3-dien-1-ols with arylboronic acids in the presence of a rhodium(I) catalyst. The reaction proceeds through the regioselective addition of organorhodium(I) species across the aryl-substituted carboncarbon double bond of the allene moiety and subsequent δ-elimination of Rh(I)OH.

Graphical abstract: Stereoselective synthesis of vinyl-substituted (Z)-stilbenes by rhodium-catalysed addition of arylboronic acids to allenic alcohols

Supplementary files

Article information

Article type
Communication
Submitted
23 May 2010
Accepted
29 Jun 2010
First published
26 Jul 2010

Org. Biomol. Chem., 2010,8, 4074-4076

Stereoselective synthesis of vinyl-substituted (Z)-stilbenes by rhodium-catalysed addition of arylboronic acids to allenic alcohols

T. Miura, H. Shimizu, T. Igarashi and M. Murakami, Org. Biomol. Chem., 2010, 8, 4074 DOI: 10.1039/C0OB00163E

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