Methodology for in Situ Protection of Aldehydes and Ketones Using Trimethylsilyl Trifluoromethanesulfonate and Phosphines: Selective Alkylation and Reduction of …

…, M Minami, Y Yoshikawa, K Watanabe…

Index: Yahata, Kenzo; Minami, Masaki; Yoshikawa, Yuki; Watanabe, Kei; Fujioka, Hiromichi Chemical and Pharmaceutical Bulletin, 2013 , vol. 61, # 12 p. 1298 - 1307

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Citation Number: 7

Abstract

A methodology for selective transformations of ketones, esters, Weinreb amides, and nitriles in the presence of aldehydes has been developed. The use of a combination of PPh 3- trimethylsilyl trifluoromethanesulfonate (TMSOTf) promotes selective transformation of aldehydes to their corresponding, temporarily protected, O, P-acetal type phosphonium salts. Because, hydrolytic work-up following ensuing reactions of other carbonyl moieties ...

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