A novel synthetic route to chiral gamma-lactams from alpha-amino acids via Rh-catalyzed intramolecular C-H insertion.
Highly functionalized gamma-lactams are key intermediates for the synthesis of numerous biologically significant natural products. We herein described the synthesis of various chiral gamma-lactams via intramolecular C-H insertion of alpha-diazo-alpha-(phenylsulfonyl)acetamides derived from alpha-amino acids, which possess various functional groups. The cyclizations were highly regio- and stereoselective to afford chiral gamma-lactam motifs in high yields.
Yoon
Cheol Hwan
CH
Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, Florida 33620-5250, USA.
Flanigan
David L
DL
Chong
Byong-Don
BD
Jung
Kyung Woon
KW
D000596:Amino Acids / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D018360:Crystallography, X-Ray; D003500:Cyclization; D007769:Lactams / Q000138:chemical synthesis*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D001391:Azo Compounds; D007769:Lactams; D012238:Rhodium