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Sodium Phenoxide-Phosphine Oxides as Extremely Active Lewis Base Catalysts for the Mukaiyama Aldol Reaction with Ketones

Manabu Hatano, Eri Takagi and Kazuaki Ishihara*

*Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan, Email: ishiharacc.nagoya-u.ac.jp

M. Hatano, E. Takagi, K. Ishihara, Org. Lett., 2007, 9, 4527-4530.

DOI: 10.1021/ol702052r (free Supporting Information)


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Abstract

A highly efficient Mukaiyama aldol reaction is catalyzed by sodium phenoxide-phosphine oxides as simple homogeneous Lewis base catalysts, which minimized competing retro-aldol reaction. Various aromatic ketones and aldimines, aldol and Mannich-type products with an α-quaternary carbon center were obtained in good to excellent yields.

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Key Words

Mukaiyama Aldol Reaction, β-Amino Acids


ID: J54-Y2007-3370