Use of 1,1'-Binaphthalene-8,8'-diol as a Chiral Auxiliary for Asymmetric Michael Addition. Application to the Syntheses of Turmeronol A and B.

Abstract

Highly diastereoselective Michael addition of lithium diorganocuprates to the half-ester of 1, 1'-binaphthalene-8, 8'-diol gave β-substituted esters with high enantiomeric excess after methanolysis. The optically active phenolic sesquiterpenes turmeronol A (1) and B(2) have been synthesized using this reaction as a key step.