Enantioselective conjugate addition of silylketene acetals to beta-enamidomalonates. Synthesis of beta-amino acid derivatives.
[reaction: see text] Conjugate addition of silylketene acetals or enolsilanes to enamidomalonates proceeds with excellent chemical efficiency and good selectivity using Cu(OTf)2 and a chiral bisoxazoline. The effect of the Lewis acid, ligand, the N-acyl substituent, and the nucleophile on yield and selectivity for the addition product have been evaluated.
Sibi
Mukund P
MP
Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105, USA. mukund.sibi@ndsu.nodak.edu
Chen
Jianxie
J
D000080:Acetals / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis*; D008314:Malonates / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
D000080:Acetals; D000596:Amino Acids; D008314:Malonates; D012821:Silanes