O??(2??Oxopyrrolidin??5??yl) trichloroacetimidates as Amidoalkylating Agents− Synthesis of (+)??Lentiginosine

AOH El??Nezhawy, HI El??Diwani…

Index: El-Nezhawy, Ahmed O. H.; El-Diwani, Hoda I.; Schmidt, Richard R. European Journal of Organic Chemistry, 2002 , # 24 p. 4137 - 4142

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Citation Number: 24

Abstract

Abstract N-α-Hydroxyalkylamides 6a, b, readily available from L-tartrate, with trichloroacetonitrile furnish O-(2-oxopyrrolidin-5-yl) trichloroacetimidates 3a, b. α-Amido- alkylation studies of 3a, b with allyl-trimethylsilane and electron-rich benzene derivatives as C-nucleophiles afforded 5-allyl-and 5-aryl-2-pyrrolidinones 2a, b, 7a, b, and 8− 10. The target compound (+)-1 and its epimer 15 were readily obtained from 1, 5-diallyl-2- ...