Highly Enantioselective Synthesis of α, α-Dialkylmalonates by Phase-Transfer Catalytic Desymmetrization

S Hong, J Lee, M Kim, Y Park, C Park…

Index: Hong, Suckchang; Lee, Jihye; Kim, Minsik; Park, Yohan; Park, Cheonhyoung; Kim, Mi-Hyun; Jew, Sang-Sup; Park, Hyeung-Geun Journal of the American Chemical Society, 2011 , vol. 133, # 13 p. 4924 - 4929

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Citation Number: 28

Abstract

A novel enantioselective synthetic method for the construction of a quaternary carbon center from malonates via phase-transfer catalytic (PTC) alkylation has been developed. The asymmetric α-alkylation of diphenylmethyl tert-butyl α-alkylmalonates with alkylating agents under phase-transfer catalysis conditions (aq 50% KOH, toluene, 0° C) in the presence of (S, S)-3, 4, 5-trifluorophenyl-NAS bromide (8) as PTC catalyst afforded the corresponding α, α ...