Organocatalytic Tandem Three-Component Reaction of Imine, Alkyl Vinyl Ketone, and Imide via aza-Baylis-Hillman Reaction

Siang-en Syu, Yu-Ting Lee, Yeong-Jiunn Jang and Wenwei Lin*

*Department of Chemistry, National Taiwan Normal University, 88, Section 4, Tingchow Road, Taipei 11677, Taiwan, Republic of China, Email: wenweilinntnu.edu.tw

S.-e. Syu, Y.-T. Lee, Y.-J. Jang, W. Lin, J. Org. Chem., 2011, 76, 2888-2891.

DOI: 10.1021/jo102143r

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Abstract

A highly chemoselective PPh₃-catalyzed three-component reaction of an imine, alkyl vinyl ketone, and phthalimide or succinimide gives various highly functional adducts with high diastereoselectivities via aza-Morita-Baylis-Hillman reactions of aryl-substituted imines and alkyl vinyl ketones followed by Michael additions of imides and then epimerization.

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Key Words

β-Amino Ketones, Protected Amines, Baylis-Hillman reaction, Multicomponent Reactions, Phthalimides

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ID: J42-Y2011-1150