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 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.