The Journal of organic chemistry

Reaction of 2, 3-Allenoates with TsNBr2 in the Presence of Base: A Facile Highly Stereoselective Synthesis of (1 E, 2 E)-3-Bromo-4-oxo-N'-tosyl-2-alkenoxylimidic …

R Shen, X Huang

Index: Shen, Ruwei; Huang, Xian Journal of Organic Chemistry, 2007 , vol. 72, # 10 p. 3961 - 3964

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Citation Number: 24

Abstract

A novel reaction pathway of 2, 3-allenoates with an electrophile (TsNBr2) in the presence of K2CO3 to produce (1 E, 2 E)-3-bromo-4-oxo-N'-tosyl-2-alkenoxylimidic acid ethyl esters is reported. The reaction proceeds in a highly stereoselective fashion. A plausible mechanism to rationalize this reaction is also proposed.