Novel Synthesis of. ALPHA.-Amino Carboxamides and Their Related Compounds via. ALPHA.-Oxo Sulfones Starting from 2, 2-Disulfonyloxiranes

S Matsumoto, M Ishii, K Kimura, K Ogura

Index: Matsumoto, Shoji; Ishii, Michiko; Kimura, Kazuto; Ogura, Katsuyuki Bulletin of the Chemical Society of Japan, 2004 , vol. 77, # 10 p. 1897 - 1903

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Citation Number: 8

Abstract

2-(Methylsulfonyl)-2-(p-tolylsulfonyl) oxiranes 1 are easily prepared by the condensation of methylthiomethyl p-tolyl sulfone (MT-sulfone) with aldehydes and the subsequent oxidation with MCPBA. They smoothly reacted with 2 molar amounts of primary or secondary amines to give α-amino carboxamides in high yield. This reaction can be suitably extended to the reaction with one molar amount of 1, n-diaminoalkanes (n= 2, 3, or 4) to form the ...