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

✍ Scribed by J. Van Betsbrugge; D. Tourwé; B. Kaptein; H. Kierkels; R. Broxterman

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
397 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

Boc-(R)-ot-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 ct-allylphenylglycine ethyl ester was enzymatically resolved using PLE. Hydroboration and oxidation of the double bond, Boc-protection and subsequent ring closure using the Mitsunobu reaction protocol gave rise to Boc-(R)-ot-phenylproline ethyl ester.

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