title: One-pot asymmetric synthesis of beta-cyanohydroxymethyl alpha-amino acid derivatives: formation of three contiguous stereogenic centers.
abstract: [reaction: see text] One-pot asymmetric Mannich-hydrocyanation reactions are described. Reaction of unmodified aldehydes with N-PMP-protected alpha-imino ethyl glyoxylate in the presence of catalytic amounts of L-proline followed by the addition of Et(2)AlCN provided highly enantiomerically pure beta-cyanohydroxymethyl alpha-amino acid derivatives possessing three contiguous stereogenic centers as single diastereomers (93-99% ee). Control of reaction temperature during the cyanation step directed whether cyclization of the products to lactones occurred.
authors.affiliation: The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Shin-ichi
authors.initials: S
authors.lastname: Watanabe
authors.forename: Armando
authors.initials: A
authors.lastname: Córdova
authors.forename: Fujie
authors.initials: F
authors.lastname: Tanaka
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D007783:Lactones; D011392:Proline