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α-（N-甲酰基）烷基铜酸盐与对映体富集的炔丙基亲电试剂的反应：对映体富集的3-吡咯啉的合成

Reaction of alpha-(N-carbamoyl)alkylcuprates with enantioenriched propargyl electrophiles: synthesis of enantioenriched 3-pyrrolines.

作者信息

Dieter R Karl, Chen Ningyi, Gore Vinayak K

机构信息

Howard L. Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634-0973, USA.

出版信息

J Org Chem. 2006 Nov 10;71(23):8755-60. doi: 10.1021/jo061442h.

DOI:10.1021/jo061442h
PMID:17081003
Abstract

Enantioenriched propargyl mesylates or perfluorobenzoates react with alpha-(N-carbamoyl)alkylcuprates to afford scalemic alpha-(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.

摘要

对映体富集的炔丙基甲磺酸酯或全氟苯甲酸酯与α-(N-甲酰基)烷基铜酸盐反应，得到具有对映体纯度的α-(N-甲酰基)丙二烯，该丙二烯经过N-Boc脱保护和AgNO₃促进的环化反应，得到N-烷基-3-吡咯啉。在最佳条件下进行合成序列时，相对于通过末端炔烃不对称加成到醛制备的起始炔丙醇，对映体纯度没有损失。

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