A simple and practical access to enantiopure 2,3-diamino acid derivatives

被引:46
作者
Zhou, XT [1 ]
Lin, YR [1 ]
Dai, LX [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Organomet Chem Lab, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0957-4166(99)00052-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
dEnantiomerically pure (4R,5R)- and (4S,5S)-2-imidazolines 5 were conveniently obtained on a gram scale. These can be converted into enantiopure (2R,3R)-2,3-diamino ester 6 or 2,3-diamino alcohol 7 by hydrolysis or reduction. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:855 / 862
页数:8
相关论文
共 39 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]   Cycloadditions of aromatic imines to enantiomerically pure stabilized azomethine ylids:: Construction of threo (2S,3R)-3-aryl-2,3-diamino acids [J].
Alker, D ;
Harwood, LM ;
Williams, CE .
TETRAHEDRON LETTERS, 1998, 39 (5-6) :475-478
[3]   SYNTHESIS OF L-QUISQUALIC ACID - A GENERAL-METHOD FOR ENANTIO-EFFICIENT SYNTHESIS OF BETA-AMINOALANINE DERIVATIVES [J].
BALDWIN, JE ;
ADLINGTON, RM ;
BIRCH, DJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (05) :256-257
[4]   SYNTHESIS OF L-BETA-(ISOXAZOLIN-5-ONE-2-YL)-ALANINE - A NOVEL METHOD FOR THE SYNTHESIS OF N-SUBSTITUTED 3,4-UNSUBSTITUTED ISOXAZOLIN-5-ONES [J].
BALDWIN, JE ;
ADLINGTON, RM ;
BIRCH, DJ .
TETRAHEDRON LETTERS, 1985, 26 (48) :5931-5934
[5]  
BONATI F, 1973, GAZZ CHIM ITAL, V103, P373
[6]   STEREOSELECTIVE SYNTHESIS OF 2,3-DIAMINO ACIDS - 2,3-DIAMINO-4-PHENYLBUTANOIC ACID [J].
DUNN, PJ ;
HANER, R ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17) :5017-5025
[7]   STERIC CONFIGURATION OF THE ALPHA,BETA-DIAMINOBUTYRIC ACID ISOLATED FROM THE ANTIBIOTIC GLUMAMYCIN [J].
FUJINO, M ;
INOUE, M ;
UEYANAGI, J ;
MIYAKE, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1961, 34 (05) :740-740
[8]   ON GLUMAMYCIN A NEW ANTIBIOTIC .V. STERIC CONFIGURATION OF ALPHA, BETA-DIAMINOBUTYRIC ACID [J].
FUJINO, M ;
INOUE, M ;
UEYANAGI, J ;
MIYAKE, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1965, 38 (04) :515-+
[9]   An efficient asymmetric route to 2,3-diaminobutanoic acids [J].
Han, HS ;
Yoon, J ;
Janda, KD .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :2045-2048
[10]  
HARTMAN GD, 1988, ORG SYNTH, V50-9, P620