Lewis acid catalyzed highly stereoselective domino-ring-opening cyclization of activated aziridines with enolates: synthesis of functionalized chiral γ-lactams.
A highly enantio- and diastereoselective Lewis acid catalyzed S(N)2-type ring opening followed by cyclization of aziridines with active methylene carbon nucleophiles to functionalized chiral γ-lactams in a domino fashion has been developed. γ-Lactams have been desulfonated and decarboxylated, providing pyrrolidone-3-carboxylate and N-tosylpyrrolidinone derivatives, respectively, in good yields.
Ghorai
Manas K
MK
Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India. mkghorai@iitk.ac.in
Tiwari
Deo Prakash
DP
D000143:Acids / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000143:Acids; D001388:Aziridines; D007659:Ketones; D007769:Lactams