Indium-Mediated Addition of gamma-Substituted Allylic Halides to N-Aryl alpha-Imino Esters: Diastereoselective Production of beta,beta '-Disubstituted alpha-Amino Acid Derivatives with Two Contiguous Stereocenters

[摘要]：Chelation-controlled Barbier-type indium-mediated addition of gamma-substituted allylic halides to N-aryl (including N-PMP) a-imino- and N-acylhydrazono esters and highly diastereoselective tailoring of functionalized g,d-unsaturated beta,beta'-disubstituted N-aryl a-amino acid derivatives, bearing two contiguous stereocenters is reported. Further N-allylation of the resulting ?,d-unsaturated beta,beta'-disubstituted N-aryl amino acid derivatives followed by ring closing metathesis (RCM) led to the synthesis of 2,3-disubstituted N-aryltetrahydropyridine derivatives bearing two contiguous stereocenters. The stereochemistry of the key products was unequivocally established from X-ray structure analyses.

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