Efficient asymmetric synthesis of quaternary (E)-vinylglycines by deconjugative alkylation of dehydroamino acids.
A two-step protocol for the asymmetric synthesis of protected quaternary (E)-vinylglycines from simple aldehydes is reported. The key step is a regiocontrolled deconjugative asymmetric alkylation of dehydroamino acids, giving the targets as single geometric isomers with high diastereoselectivity (92-96% de). The products can be converted to valuable quaternary beta-amino alcohols by chemoselective reduction. [reaction: see text].
Jones
Matthew C
MC
School of Chemistry, University of Leeds, Leeds LS2 9JT, UK.
Marsden
Stephen P
SP
Muñoz Subtil
Dulce M
DM
D000447:Aldehydes / Q000138:chemical synthesis; D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000447:Aldehydes; D000596:Amino Acids; C006507:vinylglycine; D005998:Glycine