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Asymmetric Mukaiyama Aldol Reaction of Nonactivated Ketones Catalyzed by allo-Threonine-Derived Oxazaborolidinone

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journal contribution
posted on 06.11.2008, 00:00 by Shinya Adachi, Toshiro Harada
Asymmetric Mukaiyama aldol reaction of nonactivated ketones is realized for the first time by using an oxazaborolidinone catalyst derived from O-benzoyl-N-tosyl-allo-threonine. By employing a dimethylsilyl ketene S,O-acetal as a nucleophile, a variety of acetophenone derivatives afford the corresponding tertiary β-hydroxy carbonyl compounds with high enantioselectivity up to 98% ee.