Regio- and Stereoselective α-Allylation with Enolates Prepared from N–C Axially Chiral Thiolactam and Lactam

Abstract

The reaction of allyl bromide derivatives with the enolate prepared from enantioenriched N−C axially chiral N-(2,5di-tert-butylphenyl)-3,4-dihydroquinolin-2-one (lactam) and -thione (thiolactam) proceeded in a completely regio-and stereoselective manner to afford S N 2 and S N 2′-like products, respectively. Furthermore, through the conversion of thiolactam to lactam, the regiodivergent and stereoselective synthesis of N−C axially chiral lactams bearing a chiral tertiary α-carbon was achieved.