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Synlett 2010(10): 1511-1514
DOI: 10.1055/s-0029-1219933
DOI: 10.1055/s-0029-1219933
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Anionic Cyclization of N-(trans-2,3-Diphenylaziridin-1-yl)imines: Its Application to Sesquiterpene Synthesis via Consecutive Carbon-Carbon Bond-Formation Approach
Further Information
Received
8 March 2010
Publication Date:
10 May 2010 (online)
Publication History
Publication Date:
10 May 2010 (online)
Abstract
The anionic consecutive carbon-carbon (CC-C) bond formation can be achieved by the anionic cyclizations of N-(trans-2,3-diphenylaziridin-1-yl)imines with alkyllithiums. The synthetic efficiency of CC-C bond-formation approach has been demonstrated in the synthesis of dl-pentalenene and dl-cedrone.
Key words
anionic cyclization - N-aziridinylimine - sesquiterpene - dl-pentalenene - dl-cedrone
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References
The major stereoisomer is depicted in compound 10 and 11. In Scheme [5] , the minor isomer is shown as 10b.