Chiral oxazolidinones from N-Boc derivatives of β-amino alcohols. Effect of a N-methyl substituent on reactivity and stereoselectivity

Article abstract of DOI:10.1016/0040-4039(93)88071-P

Treatment of N-tert-butoxycarbonyl derivatives of homochiral β-amino alcohols with p-toluenesulfonyl chloride affords 2-axazolidinones. These heterocycles were produced by intramolecular nucleophilic attack of the carbamate moiety in an intermediate tosylate. The presence of a N-methyl substituent enhanced the cyclization rate and this effect was studied by AMI calculations.