Stereoselective synthesis of non-proteinogenic amino acids

被引:6
作者
Bowler, AN [1 ]
Doyle, PM [1 ]
Hitchcock, PB [1 ]
Young, DW [1 ]
机构
[1] UNIV SUSSEX,CPES,SUSSEX CTR BIOMOL DESIGN & DRUG DEV,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4020(97)00666-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The lactam enolate of the protected pyroglutamic acid ester (1) has been shown to react with activated imines to yield optically pure derivatives of non-proteinogenic amino acids. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:10545 / 10554
页数:10
相关论文
共 21 条
[1]   1,2-BENZISOTHIAZOLE 1,1-DIOXIDES - SYNTHESIS OF 3-ALKYL-(OR ARYL-)1,2-BENZISOTHIAZOLE 1,1-DIOXIDES AND RELATED COMPOUNDS [J].
ABRAMOVITCH, RA ;
SMITH, EM ;
HUMBER, M ;
PURTSCHERT, B ;
SRINIVASAN, PC ;
SINGER, GM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (22) :2589-2594
[2]   ARYLSULFONYLIMINE - DARSTELLUNG EIGENSCHAFTEN UND REAKTIVITAT [J].
ALBRECHT, R ;
KRESZE, G ;
MLAKAR, B .
CHEMISCHE BERICHTE-RECUEIL, 1964, 97 (02) :483-&
[3]  
[Anonymous], 1992, ALDRICHIM ACTA
[4]   Stereospecific synthesis of (2S,4R)-[5,5,5-H-2(3)]leucine [J].
August, RA ;
Khan, JA ;
Moody, CM ;
Young, DW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (06) :507-514
[5]   AMINO-ACID SYNTHESIS USING (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL [J].
BALDWIN, JE ;
MIRANDA, T ;
MOLONEY, M ;
HOKELEK, T .
TETRAHEDRON, 1989, 45 (23) :7459-7468
[6]   Synthesis of agonists and antagonists for central glutamate receptors by a novel 'ring switching' strategy [J].
Bowler, AN ;
Dinsmore, A ;
Doyle, PM ;
Young, DW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (09) :1297-1306
[7]   SYNTHESIS OF POTENTIAL AGONISTS AND ANTAGONISTS FOR CENTRAL GLUTAMATE RECEPTORS BY A NOVEL RING SWITCHING PROCESS [J].
BOWLER, AN ;
DOYLE, PM ;
YOUNG, DW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (05) :314-316
[8]   SYNTHESIS OF NON-PROTEINOGENIC AMINO-ACIDS WITH 3 CHIRAL CENTERS [J].
BOWLER, AN ;
DOYLE, PM ;
HITCHCOCK, PB ;
YOUNG, DW .
TETRAHEDRON LETTERS, 1991, 32 (23) :2679-2682
[9]   CHEMISTRY OF OXAZIRIDINES .1. SYNTHESIS AND STRUCTURE OF 2-ARENESULFONYL-3-ARYLOXAZIRIDINES - NEW CLASS OF OXAZIRIDINES [J].
DAVIS, FA ;
LAMENDOLA, J ;
NADIR, U ;
KLUGER, EW ;
SEDERGRAN, TC ;
PANUNTO, TW ;
BILLMERS, R ;
JENKINS, R ;
TURCHI, IJ ;
WATSON, WH ;
CHEN, JS ;
KIMURA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (06) :2000-2005
[10]   TITANIUM ENOLATES FROM PYROGLUTAMATES - EXCLUSIVE FORMATION OF 4-ALPHA ALDOL ADDUCTS [J].
DIKSHIT, DK ;
BAJPAI, SN .
TETRAHEDRON LETTERS, 1995, 36 (18) :3231-3232