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

Autor:	Bernard Kaptein, R. Broxterman, H. Kierkels, Dirk Tourwé, J. Van Betsbrugge
Rok vydání:	1997
Předmět:	chemistry.chemical_classification Double bond Organic Chemistry Ring (chemistry) Biochemistry Catalysis Benzaldehyde Hydroboration chemistry.chemical_compound Hydrolysis chemistry Yield (chemistry) Drug Discovery Organic chemistry Mitsunobu reaction
Zdroj:	Tetrahedron. 53:9233-9240
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(97)00521-8
Popis:	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-protection and subsequent ring closure using the Mitsunobu reaction protocol gave rise to Boc-(R)-α-phenylproline ethyl ester.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::15faae944ed30040b356431f64b084bf https://doi.org/10.1016/s0040-4020(97)00521-8 Zobrazit plný text záznamu Full Text from ScienceDirect