Optical Resolution of 7-Oxabicyclohept-2-ene Derivatives. Diastereoselectivity in the Formation of Cyanohydrine-Brucine Complexes

Article abstract of DOI:10.1002/hlca.19840670629

A new, practical method for the optical resolution of bicyclic ketones is illustrated by the preparation of (+)-(1R,4R)-7-oxabicyclo<2.2.1>hept-5-en-2-one ((+)-1) and (+)-(1R,2S,4R)-2-cyano-7-oxabicyclo<2.2.1>hept-5-en-2-yl acetate ((+)-4).It involves the diastereoselective formation of a brucine complex with the corresponding cyanhydrine mixture.