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Synthesis 2004(9): 1321-1324  
DOI: 10.1055/s-2004-822379
PAPER
© Georg Thieme Verlag Stuttgart · New York

Platinum-Catalyzed Tandem Diboration/Intramolecular Allylboration: Diastereoselective Access to Cyclohexanes Bearing 1,3-Diols

C. Eric Ballard, James P. Morken*
Department of Chemistry, Venable and Kenan Laboratories, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina, 27599-3290, USA
Fax: +1(919)9622388; e-Mail: morken@unc.edu;
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Publication History

Received 15 April 2004
Publication Date:
18 May 2004 (online)

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Abstract

A tandem reaction sequence consisting of platinum-catalyzed diboration of 1,3-dienes followed by intramolecular allylboration and oxidative hydrolysis has been developed for constructing cyclic structures that bear a 1,3-diol. This methodology has proven effective for synthesizing cyclohexanes from dienals in good yields (44-64%) to generate diols containing two new vicinal stereocenters, one of which is quaternary. The products are obtained in high regio- and diastereomeric ratios (>19:1). A preexisting stereo­center on the substrate can provide high levels of asymmetric induction in the product.

Key words

diboration - diene - platinum - allylboration - quaternary stereocenter