Abstract
AbstractReaction of rac‐warfarin, (−)‐(1S,2R,4R)‐endo‐1,4,5,6,7,7‐hexachlorobicyclo[2.2.1]hept‐5‐ene‐2‐ carboxylic acid [(−)‐HCA] and carbodiimide reagents gave two noncyclic ketonic diastereoisomeric derivatives whereas rac‐warfarin and (−)‐HCA acid chloride with 4‐(dimethylamino)pyridine gave four cyclic hemiketal diastereoisomeric ester derivatives. The structure and stereochemistry of diastereoisomeric esters prepared from warfarin and p‐chlorowarfarin were determined from 1H‐ and 13C‐NMR spectra, mass spectra, and hydrolysis to warfarin and p‐chlorowarfarin enantiomers. The structure and stereochemistry of one of the cyclic hemiketal diastereoisomeric derivatives of warfarin are supported by an X‐ray crystallographic determination. Mechanisms for the formation of all products are proposed. © 1994 Wiley‐Liss, Inc.
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