α-Allyl-α-aryl α-amino esters in the asymmetric synthesis of acyclic and cyclic amino acid derivatives by alkene metathesis.
Allylating agents were explored for the asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem N-alkylation/π-allylation. Cross-metathesis of the tandem product was developed to provide allylic diversity not afforded in the parent reaction; the synthesis of homotyrosine and homoglutamate analogues was completed. Cyclic α-amino acid derivatives could be accessed by ring-closing metathesis presenting a viable strategy to higher ring homologue of enantioenriched α-substituted proline. The eight-membered proline analogue was successfully converted to the pyrrolizidine natural product backbone.
Penn Merck High Throughput Experimentation Laboratory, Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
John M
JM
Curto
Marisa C
MC
Kozlowski
D000478:Alkylation; D000598:Amino Acids, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004952:Esters; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry
D000598:Amino Acids, Cyclic; D004952:Esters; D011763:Pyrrolizidine Alkaloids; D011392:Proline