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

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

(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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Veröffentlicht in:Chemical & pharmaceutical bulletin 1993/11/15, Vol.41(11), pp.2034-2037
Hauptverfasser: TAKEMOTO, Yoshiji, TAKEUCHI, Jun, OHRA, Taiichi, MAEZAKI, Naoyoshi, TANAKA, Tetsuaki, IWATA, Chuzo
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric synthesis
chiral cyclopropane
lactonization
mercury(II) salt
oxaspiro[5.5]undecane
regioselective ring-opening
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container_end_page 2037
container_issue 11
container_start_page 2034
container_title Chemical & pharmaceutical bulletin
container_volume 41
creator TAKEMOTO, Yoshiji
TAKEUCHI, Jun
OHRA, Taiichi
MAEZAKI, Naoyoshi
TANAKA, Tetsuaki
IWATA, Chuzo
description (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).
doi_str_mv 10.1248/cpb.41.2034
format Article
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subjects asymmetric synthesis
chiral cyclopropane
lactonization
mercury(II) salt
oxaspiro[5.5]undecane
regioselective ring-opening
title Construction of Asymmetric Quaternary Carbon Center Containing Heteroatom via Regioselective Cleavage of Cyclopropane Ring Mediated by Mercury(II) Salt
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