Synlett 2013; 24(10): 1201-1204
DOI: 10.1055/s-0033-1338838
cluster
© Georg Thieme Verlag Stuttgart · New York

Desymmetrization of Cyclohexadienones via Intramolecular Stetter Reaction to Construct Tricyclic Carbocycles

Min-Qiang Jia
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China   Fax: +86(21)54925087   Email: slyou@sioc.ac.cn
,
Shu-Li You*
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China   Fax: +86(21)54925087   Email: slyou@sioc.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 08 April 2013

Accepted after revision: 29 April 2013

Publication Date:
17 May 2013 (online)

Abstract

N-Heterocyclic carbene catalyzed desymmetrization of cyclohexadienones to construct tricyclic carbocycles via an intramolecular enantioselective Stetter reaction was realized. With 10 mol% of d-camphor-derived triazolium salt E and 10 mol% of KOAc, various substituted tricyclic carbocycles bearing a quaternary carbon stereogenic center and two contiguous stereocenters were obtained in excellent yields with up to 89% ee.

Supporting Information

 
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