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Titolo:
Diastereoselective synthesis of 2-alkylated 4-silylxyproline esters
Autore:
Sato, T; Kawasaki, S; Oda, N; Yagi, S; El Bialy, SAA; Uenishi, J; Yamauchi, M; Ikeda, M;
Indirizzi:
Kyoto Pharmaceut Univ, Kyoto 6078414, Japan Kyoto Pharmaceut Univ Kyoto Japan 6078414 eut Univ, Kyoto 6078414, Japan Univ Mansoura, Fac Pharm, Mansoura 35516, Egypt Univ Mansoura Mansoura Egypt 35516 ura, Fac Pharm, Mansoura 35516, Egypt Josai Univ, Fac Pharmaceut Sci, Sakado, Saitama 3500295, Japan Josai UnivSakado Saitama Japan 3500295 i, Sakado, Saitama 3500295, Japan
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 20, , anno: 2001,
pagine: 2623 - 2631
SICI:
1472-7781(20011021):20<2623:DSO24E>2.0.ZU;2-#
Fonte:
ISI
Lingua:
ENG
Soggetto:
ALPHA-ALKYLPROLINE DERIVATIVES; FORMAL TOTAL SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALKYLATION; ACIDS; (-)-CEPHALOTAXINE; METHYLPROLINE; MIMETICS; PEPTIDES; DESIGN;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
28
Recensione:
Indirizzi per estratti:
Indirizzo: Sato, T Kyoto Pharmaceut Univ, Kyoto 6078414, Japan Kyoto Pharmaceut UnivKyoto Japan 6078414 , Kyoto 6078414, Japan
Citazione:
T. Sato et al., "Diastereoselective synthesis of 2-alkylated 4-silylxyproline esters", J CHEM S P1, (20), 2001, pp. 2623-2631

Abstract

Treatment of the 4-silyloxy-N-Boc-L-proline methyl ester 1 with allyl bromide in the presence of LDA in THF at, -78 degreesC gives a mixture of the (2S,4R)- and (2R,4R)-2-(prop-2-enyl)-4-silyloxy-N-Boc-L-proline esters 2a and 2b in 75% combined yield in the ratio 53:47. In contrast, similar treatment of the (-)- and (+)-menthyl esters 5 and 6 gives a mixture of allylated products 7a,b and 8a,b in the ratio 75:25 and 89:11, respectively. Reactionof 6 with methyl iodide and propyl iodide also give the corresponding 2-alkylated esters 16a and 16b in a highly diastereoselective manner (94:6 and 93:7, respectively).

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 29/03/20 alle ore 15:39:28