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

The reaction of allyl bromide derivatives with the enolate prepared from enantioenriched N–C axially chiral N-(2,5-di-tert-butylphenyl)-3,4-dihydroquinolin-2-one (lactam) and -thione (thiolactam) proceeded in a completely regio- and stereoselective manner to afford SN2 and SN2′-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.