Asymmetric synthesis of quaternary alpha- and beta-amino acids and beta-lactams via proline-catalyzed mannich reactions with branched aldehyde donors.
[reaction: see text] L-Proline-catalyzed direct asymmetric Mannich reactions of N-PMP protected alpha-imino ethyl glyoxylate with various alpha,alpha-disubstituted aldehydes affords quaternary beta-formyl alpha-amino acid derivatives with excellent yields and enantioselectivities. The Mannich products are further converted to the corresponding quaternary alpha- and beta-amino acids and beta-lactams.
Chowdari
Naidu S
NS
The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Suri
Jeff T
JT
Barbas
Carlos F
CF
D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000032:analysis / Q000138:chemical synthesis*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000032:analysis / Q000138:chemical synthesis*
D000447:Aldehydes; D000596:Amino Acids; D047090:beta-Lactams; D011392:Proline