Construction of Asymmetric Quaternary Carbon Center Containing Heteroatom via Regioselective Cleavage of Cyclopropane Ring Mediated by Mercury(II) Salt

Yoshiji TAKEMOTO; Jun TAKEUCHI; Taiichi OHRA; Naoyoshi MAEZAKI; Tetsuaki TANAKA; Chuzo IWATA

doi:10.1248/cpb.41.2034

Yoshiji TAKEMOTO, Jun TAKEUCHI, Taiichi OHRA, Naoyoshi MAEZAKI, Tetsuaki TANAKA, Chuzo IWATA

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Keywords: regioselective ring-opening, mercury(II) salt, chiral cyclopropane, oxaspiro[5.5]undecane, lactonization, asymmetric synthesis

JOURNAL FREE ACCESS

1993 Volume 41 Issue 11 Pages 2034-2037

DOI https://doi.org/10.1248/cpb.41.2034

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Abstract

(6S, 7S)-1-Oxa-7-bromomethylspiro[5.5]undecanes (12 and 13) were synthesized from the optically active alkenyl sulfoxide (7). The key step involves a tandem regioselective cleavage of cyclopropane ring and stereoselective nucleophilic cyclization of the cyclopropylcarboxylic acid (11).

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