title: Lewis acid promoted highly diastereoselective Petasis Borono-Mannich reaction: efficient synthesis of optically active β,γ-unsaturated α-amino acids.
abstract: An efficient and straightforward method for the preparation of highly enantiomerically enriched β,γ-unsaturated α-amino acid derivatives by a Lewis acid promoted diastereoselective Petasis reaction of vinylboronic acid, N-tert-butanesulfinamide, and glyoxylic acid has been developed. The synthetic utilities of the approach were demonstrated by the rapid and convenient construction of challenging cyclopenta[c]proline derivatives.
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.
authors.forename: Yi
authors.initials: Y
authors.lastname: Li
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Xu
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D002073:Butanes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006038:Glyoxylates / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D000596:Amino Acids; D001897:Boronic Acids; D002073:Butanes; D006038:Glyoxylates; D058116:Lewis Acids; D013449:Sulfonamides; D014753:Vinyl Compounds; C511422:tert-butanesulfinamide; C031150:glyoxylic acid