Novel asymmetric approach to proline-derived spiro-beta-lactams.
We describe a novel asymmetric approach using Staudinger chemistry to proline-derived spiro-beta-lactams. A chiral group at C-4 of the acid chloride of proline directs the stereoselectivity of Staudinger chemistry and later is sacrificed to obtain optically active 5.4-spiro-beta-lactams. The scope, limitations, and mechanistic rationale for the observed results of Staudinger Chemistry of the acid chloride of 4-alkyl(aryl)sulfonyloxy-l-proline with imines are also discussed.
Khasanov
Alisher B
AB
Department of Chemistry Research, ChemBridge Research Laboratories and ChemBridge Corporation, 16981 Via Tazon, San Diego, California 92127, USA.
Ramirez-Weinhouse
Michele M
MM
Webb
Thomas R
TR
Thiruvazhi
Mohan
M
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D007097:Imines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis*
D007097:Imines; D047090:beta-Lactams; D011392:Proline