α-氨基酰胺类化合物的合成新方法

doi:10.3724/SP.J.1095.2013.20600

摘要/Abstract

摘要： 以三氟化硼乙醚配合物为催化剂，研究了亚胺与氨甲酰基硅烷的反应。考察了亚胺碳原子连接基团(乙基、异丙基、三氟甲基、苯乙烯基、苯基、呋喃基、噻吩基和吡啶基)对反应的影响，合成了几种α-氨基酰胺；当亚胺氮原子连接的烃基和氨甲酰基硅烷中氮原子连接的烃基为手性基团S1苯乙基和R1苯乙基时，得到了具有高度立体选择性的产物(非对映异构体比率为14∶1)，是一种不对称合成α-氨基酰胺的新方法。

关键词: 亚胺, 氨甲酰基硅烷, &, alpha, -氨基酰胺, 不对称合成

Abstract: It was found that boron trifluoride etherate was an effective catalyst for the reactions between carbamoylsilane and imines. The influences of various substitution groups(ethyl, isopropyl, trifluoromethyl, styryl, phenyl, furyl, thienyl, pyridyl) on the C-terminus of the parent iminium to the reaction have been studied and some α-aminoamides were synthesized. The stereoselectivety of the reaction was found by connecting chiral alkyl(S-1-phenylethyl) on the N-terminus of the iminium and the highly stereoselective product was obtained(diastereomer ratio of 14∶1) by connecting chiral alkyl both on the N-terminus of the iminium structure(S-1-phenylethyl) and on the N-terminus of carbamoylsilane(R-1-phenylethyl). So this is a new method for stereoselectivly synthesizing α-aminoamides.

Key words: imine, carbamoylsilane, &, alpha, &, mdash, aminoamide, asymmetric synthesis

中图分类号:

O621.3

郭文彦, 陈建新. α-氨基酰胺类化合物的合成新方法[J]. 应用化学, DOI: 10.3724/SP.J.1095.2013.20600.

GUO Wenyan1,2, CHEN Jianxin1*. A New Method for Synthesizing α-Aminoamide Compounds[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.20600.

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