A convenient synthesis of protected (R)-α-phenylproline derivatives using the Mitsunobu reaction

J Van Betsbrugge, D Tourwé, B Kaptein, H Kierkels…

Index: Van Betsbrugge; Tourwe; Kaptein; Kierkels; Broxterman Tetrahedron, 1997 , vol. 53, # 27 p. 9233 - 9240

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Citation Number: 26

Abstract

Boc-(R)-α-phenylproline ethyl ester 1 was prepared in good yield starting from racemic phenylglycine. Condensation of phenylglycine ethyl ester with benzaldehyde furnished N- benzylidene phenylglycine ethyl ester which was allylated under phase transfer catalysis conditions. After acidic hydrolysis, the resulting α-allylphenylglycine ethyl ester was enzymatically resolved using PLE. Hydroboration and oxidation of the double bond, Boc- ...