Stereospecific synthesis of 2-deuterio-3-hydroxybutanoate esters. Regiochemistry and stereochemistry of homogeneous hydrogenation with Wilkinson's catalyst

JR Mohrig, SL Dabora, TF Foster…

Index: Mohrig, Jerry R.; Dabora, Sandra L.; Foster, Ted F.; Schultz, Steve C. Journal of Organic Chemistry, 1984 , vol. 49, # 26 p. 5179 - 5182

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Citation Number: 16

Abstract

Results The synthesis of 0-(acyloxy)-a,@-unsaturated esters can be accomplished in good yield by the method of Casey and Marten8 Clean separation of the 2 and E isomers was possible on a silica gel column. The stereochemical assignments in 2a and 2b rest upon NMR shift correlation~.~,~ Protons that are cis to oxygen and carbalkoxy groups are shifted downfield. In our initial work we expected to use 2, substituted with deuterium at (2-2, as ...