Synthesis and application of chiral β-amino disulfides as ligands for the enantioselective addition of diethylzinc to aldehydes

被引:27
作者
Braga, Antonio L. [1 ]
Galetto, Fabio Z. [1 ]
Rodrigues, Oscar E. D. [2 ]
Silveira, Claudio C. [1 ]
Paixao, Marcio W. [3 ]
机构
[1] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil
[2] Ctr Univ Franciscano, Santa Maria, RS, Brazil
[3] Univ Sao Paulo, Inst Quim, Sao Paulo, Brazil
关键词
asymmetric catalysis; chiral ligands; thiols; sulfur; zinc;
D O I
10.1002/chir.20554
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new class of chiral beta-amino disulfides was synthesized from readily available and inexpensive starting materials by a straightforward method and their abilities as ligands were examined in the enantioselective addition of diethylzinc to aldehydes. Enantiomeric excesses of up to 99% have been obtained using 0.5 mol % of the chiral catalysts.
引用
收藏
页码:839 / 845
页数:7
相关论文
共 79 条
[1]   Concepts for ligand design in asymmetric catalysis: a study of chiral amino thiol ligands [J].
Anderson, JC ;
Cubbon, R ;
Harding, M ;
James, DS .
TETRAHEDRON-ASYMMETRY, 1998, 9 (19) :3461-3490
[2]  
ANDERSON JC, 1996, CHEM COMMUN, P393
[3]   SPECTROSCOPIC STUDIES ON THE BETA-HYDROXYSULFOXIMINE-CATALYZED ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES [J].
BOLM, C ;
MULLER, J .
TETRAHEDRON, 1994, 50 (15) :4355-4362
[4]   Synthesis of new chiral aliphatic amino diselenides and their application as catalysts for the enantioselective addition of diethylzinc to aldehydes [J].
Braga, AL ;
Paixao, MW ;
LUdtke, DS ;
Silveira, CC ;
Rodrigues, OED .
ORGANIC LETTERS, 2003, 5 (15) :2635-2638
[5]   Catalytic enantioselective arylation of aldehydes:: boronic acids as a suitable source of transferable aryl groups [J].
Braga, AL ;
Lüdtke, DS ;
Vargas, F ;
Paixao, MW .
CHEMICAL COMMUNICATIONS, 2005, (19) :2512-2514
[6]   New C2-symmetric chiral disulfide ligands derived from (R)-cysteine [J].
Braga, AL ;
Appelt, HR ;
Schneider, PH ;
Rodrigues, OED ;
Silveira, CC ;
Wessjohann, LA .
TETRAHEDRON, 2001, 57 (16) :3291-3295
[7]   Synthesis of new chiral imidazolidine disulfides derived from L-cystine and their application in the enantioselective addition of diethylzinc to aldehydes [J].
Braga, AL ;
Vargas, F ;
Silveira, CC ;
de Andrade, LH .
TETRAHEDRON LETTERS, 2002, 43 (13) :2335-2337
[8]   The facile synthesis of chiral oxazoline catalysts for the diethylzinc addition to aldehydes [J].
Braga, AL ;
Rubim, RM ;
Schrekker, HS ;
Wessjohann, LA ;
de Bolster, MWG ;
Zeni, G ;
Sehnem, JA .
TETRAHEDRON-ASYMMETRY, 2003, 14 (21) :3291-3295
[9]   Catalytic enantioselective aryl transfer:: asymmetric addition of boronic acids to aldehydes using pyrrolidinylmethanols as ligands [J].
Braga, AL ;
Lüdtke, DS ;
Schneider, PH ;
Vargas, F ;
Schneider, A ;
Wessjohann, LA ;
Paixao, MW .
TETRAHEDRON LETTERS, 2005, 46 (45) :7827-7830
[10]   Efficient synthesis of chiral β-seleno amides via ring-opening reaction of 2-oxazolines and their application in the palladium-catalyzed asymmetric allylic alkylation [J].
Braga, AL ;
Vargas, F ;
Sehnem, JA ;
Braga, RC .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) :9021-9024