Diastereoselectivity in the O–H Insertion Reactions of Carbenoids Derived from Phenyldiazoacetates of Chiral Alcohols. II. Comparison of Rhodium(II)- and Acid-Mediated Reactions

Abstract

Rhodium(II)- or acid-mediated decomposition of 2-diazo-2-phenylacetates of chiral alcohols in the presence of various hydroxylic compounds (ROH) results in the diastereoselective formation of 2- hydroxy-, 2-alkoxy- or 2-trialkylsiloxy-2-phenylacetates, with the acid-mediated process giving the higher diastereoselectivity.