Asymmetric Synthesis with 6??tert??Butyl??5??methoxy??6??methyl??3, 6??dihydro??2H??1, 4??oxazin??2??one as a New Chiral Glycine Equivalent: Preparation of …

…, J Pabel, A Kärtner, K Polborn…

Index: Koch, Claus-Juergen; Simonyiova, Sona; Pabel, Joerg; Kaertner, Annerose; Polborn, Kurt; Wanner, Klaus Theodor European Journal of Organic Chemistry, 2003 , # 7 p. 1244 - 1263

Full Text: HTML

Citation Number: 24

Abstract

Abstract The chiral oxazinone 2 has been developed as a new chiral glycine equivalent for the asymmetric synthesis of mono-and disubstituted α-amino acids. It is derived from the α- hydroxycarboxylic acid 1, which serves as a chiral auxiliary, and is easily accessible in enantiomerically pure form by optical resolution of the racemic compound (RS)-1. For alkylation reactions, 2 was deprotonated with sBuLi or phosphazenic base. Subsequent ...