A highly efficient Mukaiyama aldol reaction between ketones and trimethylsilyl enolates catalyzed by sodium phenoxide-phosphine oxides as simple homogeneous Lewis base catalysts (0.5-10 mol %) was developed, which minimized competing retro-aldol reaction. For a variety of aromatic ketones and aldimines, aldol and Mannich-type products with an alpha-quaternary carbon center were obtained in good to excellent yields. Up to 100 mmol scale of benzophenone and trimethylsilyl enolate with 0.5 mol % of catalyst was established in 97% yield (34.8 g).
Sodium phenoxide-phosphine oxides as extremely active Lewis base catalysts for the Mukaiyama aldol reaction with ketones. Publishing Authors By Initials
Sodium phenoxide-phosphine oxides as extremely active Lewis base catalysts for the Mukaiyama aldol reaction with ketones. Journal Published:
PUBLICATION TYPE: Research Support, Non-U.S. Gov
Journal: Organic letters
VOLUME: 9
Page Numbers: 4527-30
Journal Abbreviation: Org. Lett.
ISSN: 1523-7060
DAY: 26
MONTH: 09
YEAR: 2007
Sodium phenoxide-phosphine oxides as extremely active Lewis base catalysts for the Mukaiyama aldol reaction with ketones. Information
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LANGUAGE: eng
NlmUniqueID: 100890393
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Grant and Affiliation Information for Sodium phenoxide-phosphine oxides as extremely active Lewis base catalysts for the Mukaiyama aldol reaction with ketones.
AFFILIATION: Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan.
Country: United States
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MEDLINETA: Org Lett
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