Facile synthesis of (S,S)-1,2-diacylamides and (S,S)-1,2-diamines with C2-symmetry

被引:3
作者
Ai, Lin [1 ]
Xiao, Jichuan [1 ]
Wang, Guo [1 ]
Shen, Xiumin [1 ]
Zhang, Cong [1 ]
机构
[1] Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China
基金
中国国家自然科学基金;
关键词
(S,S)-1,2-diacylamides; (S,S)-1,2-diamines; C-2-symmetry; synthesis;
D O I
10.1080/00397910600770698
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of chiral vicinal tertiary diacylamides with C-2-symmetry was synthesized from (S)-alpha-phenylethylamine, different aromatic aldehydes, and oxalyl chloride. The diacylamides obtained were then reduced to afford chiral vicinal diamines with C-2-symmetry. We propose that the diacylamides existed in four stable conformational isomers in solution because of the dihedral angle between acylamide bonds.
引用
收藏
页码:2859 / 2875
页数:17
相关论文
共 42 条
[1]   Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine [J].
Andrey, O ;
Alexakis, A ;
Bernardinelli, G .
ORGANIC LETTERS, 2003, 5 (14) :2559-2561
[2]   RECONFIRMATION OF HIGH ENANTIOMERIC EXCESSES IN THE ENANTIOSELECTIVE TRANSFORMATION OF MESO-EPOXIDES [J].
ASAMI, M ;
INOUE, S .
TETRAHEDRON, 1995, 51 (43) :11725-11730
[3]  
BECKE AD, 1988, PHYS REV A, V37, P785, DOI DOI 10.1103/PHYS.REV.B.37-785
[4]  
BOGER M, 1985, Patent No. 2145716
[5]   KAPPA-OPIOID RECEPTOR-SELECTIVE AFFINITY LABELS - ELECTROPHILIC BENZENEACETAMIDES AS KAPPA-SELECTIVE OPIOID ANTAGONISTS [J].
CHANG, AC ;
TAKEMORI, AE ;
OJALA, WH ;
GLEASON, WB ;
PORTOGHESE, PS .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (26) :4490-4498
[6]   PRACTICAL ENANTIOSELECTIVE DIELS-ALDER AND ALDOL REACTIONS USING A NEW CHIRAL CONTROLLER SYSTEM [J].
COREY, EJ ;
IMWINKELRIED, R ;
PIKUL, S ;
XIANG, YB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5493-5495
[7]   ENANTIOSELECTIVE VICINAL HYDROXYLATION OF TERMINAL AND E-1,2-DISUBSTITUTED OLEFINS BY A CHIRAL COMPLEX OF OSMIUM TETRAOXIDE - AN EFFECTIVE CONTROLLER SYSTEM AND A RATIONAL MECHANISTIC MODEL [J].
COREY, EJ ;
JARDINE, PD ;
VIRGIL, S ;
YUEN, PW ;
CONNELL, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9243-9244
[8]  
Frisch M. J., 2004, GAUSSIAN 03 REVISION
[9]  
HALLE R, 1997, TETRAHEDRON-ASYMMETR, V8, P2101
[10]   Enantio- and diastereoselective, stereospecific Mannich-type reactions in water [J].
Hamada, T ;
Manabe, K ;
Kodayashi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (25) :7768-7769