Enantioselective Diethylzinc Addition to Aromatic Aldehydes Catalyzed by Novel Ti(IV) Complex of Three-Dentate Chiral Sulfonamide Ligands

被引:5
作者
Dabiri, Minoo [1 ]
Salehi, Peyman [2 ]
Heydari, Seddigheh [1 ]
Kozehgary, Gholamreza [1 ]
机构
[1] Shahid Beheshti Univ, Dept Chem, Fac Sci, GC, Tehran, Iran
[2] Shahid Beheshti Univ, Dept Phytochem, Med Plants & Drugs Res Inst, GC, Tehran, Iran
关键词
Aldehydes; diethylzinc; enantioselectivity; sulfonamide alcohols; DIALKYLZINC; REAGENTS; ALCOHOLS;
D O I
10.1080/00397910902900688
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of several novel three-dentate sulfonamide alcohol ligands is described, starting from camphorsulfonyl chloride. The influence of temperature and ligand structure on the asymmetric addition of dietylzinc to aromatic aldehydes has been studied. Enantioselectivities up to 76% have been obtained.
引用
收藏
页码:4350 / 4361
页数:12
相关论文
共 26 条
[1]   The direct catalytic asymmetric cross-aldol reaction of aldehydes [J].
Alcaide, B ;
Almendros, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (08) :858-860
[2]   Enantioselective diethylzinc addition to aldehydes catalyzed by Ti(IV) complex of unsymmetrical chiral bis(sulfonamide) ligands of trans-cyclohexane 1,2-diamine [J].
Bisai, Alakesh ;
Singh, Pradeep K. ;
Singh, Vinod K. .
TETRAHEDRON, 2007, 63 (03) :598-601
[3]   Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by 14-hydroxylsubstituted morphinans [J].
Dabiri, Minoo ;
Salehi, Peyman ;
Kozehgary, Gholamreza ;
Heydari, Seddigheh ;
Heydari, Akbar ;
Esfandyari, Maryam .
TETRAHEDRON-ASYMMETRY, 2008, 19 (16) :1970-1972
[4]  
Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO
[5]  
2-D
[6]   In the golden age of organocatalysis [J].
Dalko, PI ;
Moisan, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175
[7]   Chiral tertiary alcohols from a trans-1-arenesulfonyl-amino-2-isoborneolsulfonylaminocyclohexane-catalyzed addition of organozincs to ketones [J].
Forrat, VJ ;
Ramón, DJ ;
Yus, M .
TETRAHEDRON-ASYMMETRY, 2005, 16 (20) :3341-3344
[8]   Enantioselective addition of diethylzinc to aldehydes catalyzed by Titanium(IV) complexes of N-sulfonylated β-amino alcohols with four stereogenic centers [J].
Hsieh, Shengh-Siang ;
Gau, Han-Mou .
CHIRALITY, 2006, 18 (08) :569-574
[9]   Substituent effect of camphor sulfonamide ligand on the asymmetric addition of diethylzinc to aldehyde [J].
Hui, Ai-Ling ;
Zhang, Jin-Tang ;
Wang, Zhi-Yong .
ARKIVOC, 2006, :41-56
[10]  
ITO K, 1992, SYNLETT, P573