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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Zusammenfassung:(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).
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.41.2034