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

David J. Miller, Christopher J. Moody and C. Neil Morffitt

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.

Australian Journal of Chemistry 52(2) 97 - 108 (1999) doi:10.1071/C98159