EFFICIENT SYNTHESIS OF α,β-DIAMINO ACID DERIVATIVES BY In(III)-CATALYZED REGIOSELECTIVE ADDITION OF AMINES TO AZIRIDINES

被引:1
作者
Hu, Xiao-Yu [1 ,2 ]
Yang, Xiang-Yu [1 ,2 ]
Cheng, Ming [1 ,2 ]
Zhang, Qiang [1 ,2 ]
Wei, Wei [1 ,2 ]
Ji, Jian-Xin [1 ]
机构
[1] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Grad Univ, Beijing, Peoples R China
基金
美国国家科学基金会;
关键词
Amines; aziridines; catalytic synthesis; alpha; beta-diamino acid; indium(III) salt; RING-OPENING REACTIONS; OPTICALLY-ACTIVE N-ACETYL-2-METHOXYCARBONYLAZIRIDINE; ASYMMETRIC-SYNTHESIS; BETA-LACTAMS; IMINE CONDENSATION; N-TOSYLAZIRIDINES; ESTER ENOLATE; ALPHA; DIAMINES;
D O I
10.1080/00397911.2011.582977
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient catalytic method for the synthesis of alpha,beta-diamino acid derivatives has been developed via regioselective ring opening of aziridines by amines in the presence of indium( III) salt under very mild reaction conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications(R) to view the free supplemental file.
引用
收藏
页码:3403 / 3412
页数:10
相关论文
共 41 条
[1]   Stereoselective synthesis of erythro beta-substituted aspartates [J].
Antolini, L ;
Bucciarelli, M ;
Caselli, E ;
Davoli, P ;
Forni, A ;
Moretti, I ;
Prati, F ;
Torre, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) :8784-8789
[2]   Diamine containing VLA-4 antagonists [J].
Astles, PC ;
Harris, NV ;
Morley, AD .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (08) :2195-2202
[3]   Synthesis of cis and trans isomers of an isoxazoline ring-hydroxylated metabolite of Roxifiban, a platelet glycoprotein IIb/IIIa receptor antagonist [J].
Batt, DG ;
Houghton, GC ;
Daneker, WF ;
Jadhav, PK .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :8100-8104
[4]  
Bongjin M., 2005, ORG LETT, V7, P3359
[5]   PREPARATION OF 3-AMINO-4-(HYDROXYMETHYL)AZETIDIN-2-ONES FROM THE REACTION OF GLYCINE ENOLATES WITH IMINES OF A GLYCOALDEHYDE [J].
BROWN, MJ ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1933-1936
[6]   REGIOSELECTIVITY OF RING-OPENING REACTIONS OF OPTICALLY-ACTIVE N-ACETYL-2-METHOXYCARBONYLAZIRIDINE [J].
BUCCIARELLI, M ;
FORNI, A ;
MORETTI, I ;
PRATI, F ;
TORRE, G .
TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :2073-2080
[7]   Regioselective nucleophilic ring opening reactions of 2,2-disubstituted aziridines - The asymmetric synthesis of alpha,alpha-disubstituted amino acids [J].
Burgaud, BGM ;
Horwell, DC ;
Padova, A ;
Pritchard, MC .
TETRAHEDRON, 1996, 52 (40) :13035-13050
[8]   Efficient ring opening reactions of N-tosyl aziridines with amines and water in presence of catalytic amount of cerium(IV) ammonium nitrate [J].
Chakraborty, TK ;
Ghosh, A ;
Raju, TV .
CHEMISTRY LETTERS, 2003, 32 (01) :82-83
[9]   Microwave-assisted ring-opening of activated aziridines with resin-bound amines [J].
Crestey, Francois ;
Witt, Matthias ;
Frydenvang, Karla ;
Staerk, Dan ;
Jaroszewski, Jerzy W. ;
Franzyk, Henrik .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3566-3569
[10]   Application of the evans aziridination procedure to 2-substituted acrylates and cinnamates:: An expedient route to α-substituted α- and β-amino acids [J].
Dauban, P ;
Dodd, RH .
TETRAHEDRON LETTERS, 1998, 39 (32) :5739-5742