The Journal of organic chemistry

Reaction of α-(N-carbamoyl) alkylcuprates with enantioenriched propargyl electrophiles: Synthesis of enantioenriched 3-pyrrolines

RK Dieter, N Chen, VK Gore

文献索引：Dieter, R. Karl; Chen, Ningyi; Yu, Huayun; Nice, Lois E.; Gore, Vinayak K. Journal of Organic Chemistry, 2005 , vol. 70, # 6 p. 2109 - 2119

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被引用次数: 30

摘要

Enantioenriched propargyl mesylates or perfluorobenzoates react with α-(N-carbamoyl) alkylcuprates to afford scalemic α-(N-carbamoyl) allenes which undergo N-Boc deprotection and AgNO3-promoted cyclization to afford N-alkyl-3-pyrrolines. The synthetic sequence proceeds under optimal conditions with no loss of enantiopurity relative to the starting propargyl alcohols prepared by asymmetric addition of terminal alkynes to aldehydes.