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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

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, Email: mshimail.sioc.ac.cn

M. Shi, G.-N. Ma, J. Gao, J. Org. Chem., 2007, 72, 9779-9781.

DOI: 10.1021/jo701764e (free Supporting Information)


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 with alkyl vinyl ketones to give the corresponding adducts in good yields and high enantiomeric excesses under mild conditions.

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Key Words

Baylis-Hillman Reaction, Allylamines, Organocatalysis


ID: J42-Y2007-4070