Synthesis and asymmetric alkylation of glucose-derived bicyclic oxazinones: An evaluation of their use as “chiral glycines”

Abstract

We have prepared structurally novel bicyclic oxazinones based on D-glucopyranose. The lithium enolates of these compounds undergo highly diastereoselective alkylation reactions with reactive alkyl halides, in modest yields. Use of the phosphazene P4 base enhances the yields of these processes, suggesting that metal enolate aggregation is at least partly responsible for the depressed yields. The stereochemistry of the products has been unequivocally ascertained by nOe measurements and ab initio calculations.