Tributylphosphine-catalyzed Stetter reaction of N, N-dimethylacrylamide: synthesis of N, N-dimethyl-3-aroylpropionamides

JH Gong, YJ Im, KY Lee, JN Kim

Index: Gong, Ji Hyeon; Im, Yang Jin; Lee, Ka Young; Kim, Jae Nyoung Tetrahedron Letters, 2002 , vol. 43, # 7 p. 1247 - 1251

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Citation Number: 32

Abstract

Recently, mild cooperative catalytic activity of phenol derivatives in the Baylis–Hillman reaction with tributylphosphine (Bu 3 P) was reported. 3 Phenol acts as a Brφnstead acid to activate the carbonyl group of an aldehyde and a polarized alkene in the reaction. Thus, we envisioned that the use of phenol in the Baylis–Hillman reaction of N,N-dimethylacrylamide and benzaldehyde could afford the Baylis–Hillman adduct. We examined the reaction of benzaldehyde (1a) ...