New synthetic technology for the synthesis of hindered alpha-diazoketones via acyl mesylates.
[formula: see text] A mild and reliable one-pot protocol for the elaboration of sterically demanding carboxylic acids into alpha-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.
Nicolaou
K C
KC
Department of Chemistry, Scripps Research Institute, La Jolla, California 92037, USA. kcn@scripps.edu
Baran
P S
PS
Zhong
Y L
YL
Choi
H S
HS
Fong
K C
KC
He
Y
Y
Yoon
W H
WH
D007659:Ketones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008698:Mesylates / Q000737:chemistry*
D007659:Ketones; D008698:Mesylates