Synlett 2010(10): 1511-1514  
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

Sunggak Kim*a,b, Jung-Il Hwangb
a Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore
Fax: +6567911961; e-Mail: sgkim@ntu.edu.sg;
b Department of Chemistry, Korea Advanced Institute of Science and Technology, Daejeon 305-701, Korea
Further Information

Publication History

Received 8 March 2010
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.

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13

The major stereoisomer is depicted in compound 10 and 11. In Scheme  [5] , the minor isomer is shown as 10b.