Issue 18, 2010
From the journal:

Organic & Biomolecular Chemistry

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

Tomoya Miura,a   Hiroshi Shimizu,a   Tomohiro Igarashia  and  Masahiro Murakami*a  

* Corresponding authors

a Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Japan
E-mail: murakami@sbchem.kyoto-u.ac
Fax: +81 75 383 2748
Tel: +81 75 383 2747

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 carbon–carbon 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

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Article information

DOI
https://doi.org/10.1039/C0OB00163E
Article type
Communication
Submitted
23 May 2010
Accepted
29 Jun 2010
First published
26 Jul 2010

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

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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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