title: Organocatalytic synthesis of beta-alkylaspartates via beta-lactone ring opening.
abstract: Cinchona alkaloid-catalyzed reaction of ethyl glyoxylate with substituted ketenes, formed in situ, gives disubstituted beta-lactones in moderate yield and high enantiomeric excess. Subsequent azide ring opening, reduction, and ester hydrolysis allows access to chiral beta-alkyl aspartates.
authors: Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, United Kingdom. a.armstrong@imperial.ac.uk
authors: Alan
authors: A
authors: Armstrong
authors: Stephen P
authors: SP
authors: Geldart
authors: Chloe R
authors: CR
authors: Jenner
authors: James N
authors: JN
authors: Scutt
mesh_terms: D000478:Alkylation; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006868:Hydrolysis; D026581:Isoaspartic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D047090:beta-Lactams / Q000737:chemistry
chemical_list: D001386:Azides; D026581:Isoaspartic Acid; D007783:Lactones; D047090:beta-Lactams