Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers.
Minjun KimJaebong JangGoyoung ChoiSungkyun ChungChangjin LimJoonseong HurHyun Su KimYounghwa NaWoo Sung SonYoung-Ger SuhJong-Wha JungSeok-Ho KimPublished in: Molecules (Basel, Switzerland) (2018)
α-Vinyl or α-acetylenyl azacycles were easily synthesized from 7- to 9-membered lactams and 6- to 9-membered lactams via N,O-acetal trimethylsilyl (TMS) ethers. Organocopper and organostannane reagents afforded reasonable yields for the respective N-acyliminium ion vinylation and acetylenylation intermediates generated from N,O-acetal TMS ethers in the presence of a Lewis acid.