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?-Allyl-?-aryl ?-amino esters in the asymmetric synthesis of acyclic and cyclic amino acid derivatives by alkene metathesis.

ABSTRACT: Allylating agents were explored for the asymmetric synthesis of ?-allyl-?-aryl ?-amino acids by tandem N-alkylation/?-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 ?-amino acid derivatives could be accessed by ring-closing metathesis presenting a viable strategy to higher ring homologue of enantioenriched ?-substituted proline. The eight-membered proline analogue was successfully converted to the pyrrolizidine natural product backbone.

SUBMITTER: Curto JM

PROVIDER: S-EPMC4059215 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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α-Allyl-α-aryl α-amino esters in the asymmetric synthesis of acyclic and cyclic amino acid derivatives by alkene metathesis.

Curto John M JM Kozlowski Marisa C MC

The Journal of organic chemistry 20140514 11

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 e ...[more]

PMID: 24828423

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