Organic letters

Cu (I)-Catalyzed Direct Enantioselective Cross Aldol-Type Reaction of Acetonitrile

Y Suto, R Tsuji, M Kanai, M Shibasaki

Index: Suto, Yutaka; Kumagai, Naoya; Matsunaga, Shigeki; Kanai, Motomu; Shibasaki, Masakatsu Organic Letters, 2003 , vol. 5, # 17 p. 3147 - 3150

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Citation Number: 104

Abstract

Direct catalytic enantioselective cross aldol-type reaction of an acetate surrogate was developed using Cu alkoxide-chiral phosphine complexes as catalysts. Chemoselective activation and deprotonation of the donor substrate (acetonitrile) by the soft metal alkoxide in a strongly donating solvent (HMPA) are key to success in this reaction. Useful chemical yields and promising enantioselectivities are produced using either DTBM-SEGPHOS or a ...