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Synthesis of γ,δ-unsaturated 6-hydroxy substituted α-amino acids by palladium-catalyzed alkylation of monoepoxydienes

✍ Scribed by Angel Mazón; Carmen Nájera; Jesús Ezquerra; Concepción Pedregal

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
215 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Monoepoxydienes 1, derived from =cyclic and cyclic conjugated dienes, react under neutral conditions with the benzophenone imin¢ of 81ycine nitrile 4 in the presence of a catalytic amount of Pd(PPh3)4 (5% mol) to afford the cou~pondin8 unsaturated 6-hydroxy substituted ct-amino acids S in a regio (1,4-addition) and s~seleetive manner. However, the beuzophenoae imine of glycine ethyl ester 2 only react with butadieue monoepoxide to furnish regio and stereoselectively ethyl (4E)-6-hydroxy-2-(diphenylmethyleue)amino-4-hexenoate (3) a precursor of a bulgecinine diastereomer.

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