New synthetic technology for the synthesis of hindered α-diazoketones via acyl mesylates

KC Nicolaou, PS Baran, YL Zhong, HS Choi…

Index: Nicolaou; Baran, Phil S.; Zhong, Yong-Li; Choi, Ha-Soon; Fong, Kin Chiu; He, Yun; Yoon, Won Hyung Organic Letters, 1999 , vol. 1, # 6 p. 883 - 886

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Citation Number: 27

Abstract

A mild and reliable one-pot protocol for the elaboration of sterically demanding carboxylic acids into α-diazoketones via acyl mesylates has been developed. Aside from delineating the reaction parameters which render this strategy quite general for hindered carboxylic acids, we have directly proven the existence of the fleeting acyl mesylate group as the reactive species in these reactions and shed light onto the differing mechanisms which ...