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Communication | Special issue | Vol 77, No. 2, 2009, pp.787-791
Published online, 2nd October, 2008
DOI: 10.3987/COM-08-S(F)69
Construction of Cyclopentyl Carbinols from ω-Tosyloxy-1-alkenyl Boronate Esters and Grignard Reagents

Yuichi Kobayashi,* Moriteru Asano, and Yohei Kiyotsuka

*Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan

Abstract

Addition of RMgCl (R = n-Bu, Ph) to pinacol esters of 6-tosyloxy-1-alkenyl boronic acids at -78 °C gave the borates, which upon warming to room temperature underwent migration of R on boron to C(1) carbon and concomitant ring construction C-C bond formation between C(2) and C(6), eventually producing cyclopentyl alkyl (or aryl) carbinols after oxidative workup of the borane intermediates with 35% H2O2. Eight examples are presented and the reaction was applied to construction of a cyclohexyl carbinol.