Organic Letters p. 883 - 886 (1999)
Update date:2022-08-29
Topics:
Nicolaou
Baran, Phil S.
Zhong, Yong-Li
Choi, Ha-Soon
Fong, Kin Chiu
He, Yun
Yoon, Won Hyung
(equation presented) 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 are operative in the activation of hindered and simple carboxylic acids with methanesulfonyl chloride.
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