Ligand-Controlled, Complementary Stereoselectivity in the Platinum-Catalyzed Intramolecular Silaboration of Alkenes

Toshimichi Ohmura, Hideki Furukawa, and Michinori Suginome*
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan
J. Am. Chem. Soc., 2006, 128 (41), pp 13366–13367
DOI: 10.1021/ja065588+
Publication Date (Web): September 27, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, suginome@sbchem.kyoto-u.ac.jp

Abstract

Abstract Image

An intramolecular silaboration of borylsilanyl homoallyl ethers was achieved using a platinum catalyst, giving 1-oxa-2-silacyclopentanes in high yields. The stereoselectivity of the reactions of sec-homoallyl ethers strongly depended on the phosphorus ligand of the platinum catalysts used. The platinum complex bearing the PCyPh2 ligand was found to be the most trans-selective catalyst (trans/cis = 81:19−92:8), whereas a highly cis-selective cyclization was achieved using a platinum catalyst having tris(2,4-di-tert-butylphenyl)phosphite ligand (trans/cis = 8:92−6:94). The synthetic utility of the intramolecular silaboration was demonstrated by the complementary synthesis of a pair of diastereomers of 6-methylheptane-1,3,5-triol.

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History

  • Published In Issue October 18, 2006
  • Received August 2, 2006

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