Chiral phosphoramide-catalyzed aldol additions of ketone trichlorosilyl enolates. Mechanistic aspects

…, X Su, KT Wong, Y Nishigaichi

Index: Denmark, Scott E.; Su, Xiping; Nishigaichi, Yutaka; Coe, Diane M.; Wong, Ken-Tsung; Winter, Stephen B. D.; Choi, Jun Young Journal of Organic Chemistry, 1999 , vol. 64, # 6 p. 1958 - 1967

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Citation Number: 61

Abstract

The mechanism of the catalytic, enantioselective addition of trichlorosilyl enolates to aldehydes has been investigated. Kinetic studies using ReactIR and rapid injection NMR (RINMR) spectroscopy have confirmed the simultaneous operation of dual mechanistic pathways involving either one or two phosphoramides bound to a siliconium ion organizational center. This mechanistic dichotomy was initially postulated on the basis of ...