One-pot asymmetric synthesis of beta-cyanohydroxymethyl alpha-amino acid derivatives: formation of three contiguous stereogenic centers.
[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.
Watanabe
Shin-ichi
S
The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Córdova
Armando
A
Tanaka
Fujie
F
Barbas
Carlos F
CF
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
D000447:Aldehydes; D000596:Amino Acids; D007783:Lactones; D011392:Proline