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Catalytic Asymmetric Aza-Morita-Baylis-Hillman Reaction of Methyl Acrylate: Role of a Bifunctional La(O-iPr)3/Linked-BINOL Complex

Takafumi Yukawa, Bianca Seelig, Yingjie Xu, Hiroyuki Morimoto, Shigeki Matsunaga*, Albrecht Berkessel and Masakatsu Shibasaki

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo 7-3-1, Bunkyo-ku, Tokyo 113-0033, Japan, Email: smatsunamol.f.u-tokyo.ac.jp

T. Yukawa, B. Seelig, Y. Xu, H. Morimoto, Y. Xu, H. Morimoto, S. Matsunaga, A. Berkessel, M. Shibasaki, J. Am. Chem. Soc., 2010, 132, 11988-11992.

DOI: 10.1021/ja103294a (free Supporting Information)


Abstract

A La(O-iPr)3/(S,S)-TMS-linked-BINOL complex possessing bifunctional Lewis acid and Brønsted base properties in combination with an achiral nucleophilic organocatalyst efficiently promoted a catalytic asymmetric aza-Morita-Baylis-Hillman reaction of unactivated methyl acrylate with a broad range of N-diphenylphosphinoyl imines.

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Key Words

Aza-Morita-Baylis-Hillman Reaction, allylic amines


ID: J48-Y2010-2490