A New Method for Synthesizing α-Aminoamide Compounds

doi:10.3724/SP.J.1095.2013.20600

Chinese Journal of Applied Chemistry

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A New Method for Synthesizing α-Aminoamide Compounds

GUO Wenyan^1,2, CHEN Jianxin^1*

(1.College of Chemistry and Material Science,Shanxi Normal University,Linfen 041004,China;
2.Modern College of Arts and Science，Shanxi Normal University,Linfen 041000,China)

Received:2012-12-24 Revised:2013-02-22 Published:2013-10-10 Online:2013-10-10

Abstract

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

CLC Number:

O621.3

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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A New Method for Synthesizing α-Aminoamide Compounds

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