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Org Lett. 2014 Apr 4;16(7):1948-51. doi: 10.1021/ol500506t. Epub 2014 Mar 25.

Asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem alkylation/π-allylation of α-iminoesters.

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1
Department of Chemistry, Penn Merck High Throughput Experimentation Laboratory, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.

Abstract

The first asymmetric synthesis of α-allyl-α-aryl α-amino acids by means of a three-component coupling of α-iminoesters, Grignard reagents, and cinnamyl acetate is reported. Notably, the enolate from the tandem process provides a much higher level of reactivity and selectivity than the same enolate generated via direct deprotonation, presumably due to differences in the solvation/aggregation state. A novel method for removal of a homoallylic amine protecting group delivers the free amine congeners. The α-allyl group offers a means to generate further valuable α-amino acid structures as exemplified by ring closing metathesis to generate a higher ring homologue of α-aryl-proline.

PMID:
24666394
PMCID:
PMC3983326
DOI:
10.1021/ol500506t
[Indexed for MEDLINE]
Free PMC Article
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