Desymmetrization of Cyclohexadienones via Intramolecular Stetter Reaction to Construct Tricyclic Carbocycles

Min-Qiang Jia; Shu-Li You

doi:10.1055/s-0033-1338838

Synlett, Table of Contents

Synlett 2013; 24(10): 1201-1204
DOI: 10.1055/s-0033-1338838

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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

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Abstract

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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.

Key words

camphor - desymmetrization - N-heterocyclic carbene - organocatalysis - Stetter reaction

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References

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