The Journal of Organic Chemistry

Diastereoselective sulfenylation reactions employing N-phenylthio lactams under nonbasic conditions

LJ Wilson, DC Liotta

Index: Wilson, Lawrence J.; Liotta, Dennis C. Journal of Organic Chemistry, 1992 , vol. 57, # 7 p. 1948 - 1950

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Citation Number: 23

Abstract

Summary: Silyl enol ethers and silyl ketene acetals react with sulfenamides in the presence of trimethylsilyl triflate to give the corresponding trans-sulfenylated ketones and lactones. ... We have recently demonstrated the utility of the 2- phenylthio group for controlling the stereoselectivity of nitrogen glycosylation reactions used in the synthesis of the anti-HIV nucleoside, D4T (3, Scheme I).l In order for this overall approach to be successful, we required a reagent that would ...

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