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Chiral Bifunctional Organocatalysts in Asymmetric Aza-Morita−Baylis−Hillman Reactions of Ethyl (Arylimino)acetates with Methyl Vinyl Ketone and Ethyl Vinyl Ketone

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Min Shi,*^† Guang-Ning Ma,^‡ and Jun Gao^†

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, and School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 MeiLong Road, Shanghai 200237, China %mshi@mail.sioc.ac.cn

J. Org. Chem., 2007, 72 (25), pp 9779–9781

DOI: 10.1021/jo701764e

Publication Date (Web): November 8, 2007

Address correspondence to this author. Fax: 86-21-64166128.

†

Chinese Academy of Sciences.

‡

East China University of Science and Technology.

Abstract

The bifunctional chiral phosphine Lewis base (R)-2‘-diphenylphosphino-[1,1‘-binaphthalene]-2-ol is an effective organocatalyst in the asymmetric aza-MBH reaction of ethyl (arylimino)acetates 1 with MVK and EVK to give the corresponding adducts in moderate to good yields and good to high enantiomeric excesses under mild conditions.

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Published In Issue December 07, 2007
Received August 13, 2007

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Note

Chiral Bifunctional Organocatalysts in Asymmetric Aza-Morita−Baylis−Hillman Reactions of Ethyl (Arylimino)acetates with Methyl Vinyl Ketone and Ethyl Vinyl Ketone

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Asymmetric Morita-Baylis-Hillman Reaction of Arylaldehydes with 2-Cyclohexen-1-one Catalyzed by Chiral Bis(Thio)urea and DABCO

Bifunctional Organocatalysts for Enantioselective aza-Morita−Baylis−Hillman Reaction

Chiral Phosphine Lewis Bases Catalyzed Asymmetric aza-Baylis−Hillman Reaction of N-Sulfonated Imines with Activated Olefins

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