Organocatalytic synthesis of beta-alkylaspartates via beta-lactone ring opening.
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.
Armstrong
Alan
A
Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, United Kingdom. a.armstrong@imperial.ac.uk
Geldart
Stephen P
SP
Jenner
Chloe R
CR
Scutt
James N
JN
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
D001386:Azides; D026581:Isoaspartic Acid; D007783:Lactones; D047090:beta-Lactams