Highly Diastereoselective Deprotonation and Substitution of Chiral 5,6-Dihydro-4H-1,2-oxazines

Article abstract of DOI:10.1021/jo00251a050

Deprotonation of the chiral 1,2-oxazine 1 by n-butyllithium provides a carbanion which reacts highly diastereoselectively with electrophiles affording the substituted 1,2-oxazines 2.The overall substitution occurs under retention of configuration in most cases investigated.These remarkable results are in accord with recent ab initio calculations.