Stereochemistry of 1, 2-elimination reactions at the E2–E1cB interface—tert-butyl 3-tosyloxybutanoate and its thioester

…, JK Anderson, SR Anderson, RL Fimmen…

Index: Mohrig, Jerry R.; Alberg, David G.; Cartwright, Craig H.; Pflum, Mary Kay H.; Aldrich, Jeffrey S.; Anderson, J. Kyle; Anderson, Shelby R.; Fimmen, Ryan L.; Snover, Amy K. Organic and Biomolecular Chemistry, 2008 , vol. 6, # 9 p. 1641 - 1646

Full Text: HTML

Citation Number: 9

Abstract

Experimental data on the stereoselectivity of base-catalyzed 1, 2-elimination reactions that produce conjugated carbonyl compounds are scarce in spite of the importance of these reactions in organic and biochemistry. As part of a comprehensive study in this area, we have synthesized stereospecifically-deuterated β-tosyloxybutanoate esters and thioesters and studied the stereoselectivity of their elimination reactions under non-ion pairing ...