Asymmetric cyanosilylation of aldehydes catalyzed by novel organo-catalysts

被引:92
作者
Wen, YH [1 ]
Huang, X [1 ]
Huang, JL [1 ]
Xiong, Y [1 ]
Qin, B [1 ]
Feng, XM [1 ]
机构
[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China
关键词
proline-based N; N; '-dioxide; aldehydes; organocalalyst; cyallosilylation; enantioselectivity;
D O I
10.1055/s-2005-872692
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel proline-based N,N'-dioxide, which is easily prepared from inexpensive chemicals, serves as an effective catalyst for enantioselective cyanosilylation of aldehydes ill Lip to 73% ee.
引用
收藏
页码:2445 / 2448
页数:4
相关论文
共 51 条
[1]   Catalytic asymmetric synthesis of O-acetyl cyanohydrins from KCN, Ac2O and aldehydes [J].
Belokon, YN ;
Gutnov, AV ;
Moskalenko, MA ;
Yashkina, LV ;
Lesovoy, DE ;
Ikonnikov, NS ;
Larichev, VS ;
North, M .
CHEMICAL COMMUNICATIONS, 2002, (03) :244-245
[2]   ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF ALDEHYDES [J].
BOLM, C ;
MULLER, P .
TETRAHEDRON LETTERS, 1995, 36 (10) :1625-1628
[3]   Enantioselective trimethylsilylcyanation of aromatic aldehydes catalyzed by titanium alkoxide-chiral o-hydroxyarylphosphine oxides complexes [J].
Brunel, JM ;
Legrand, O ;
Buono, G .
TETRAHEDRON-ASYMMETRY, 1999, 10 (10) :1979-1984
[4]   BIO-ORGANIC SYNTHESIS OF OPTICALLY-ACTIVE CYANOHYDRINS AND ACYLOINS [J].
BRUSSEE, J ;
ROOS, EC ;
VANDERGEN, A .
TETRAHEDRON LETTERS, 1988, 29 (35) :4485-4488
[5]   NMR MEASUREMENTS AND SEMIEMPIRICAL CALCULATIONS IN A 1ST APPROACH TO ELUCIDATE THE MECHANISM OF ENANTIOSELECTIVE CYANOHYDRIN FORMATION CATALYZED BY CYCLO-(S)-PHE-(S)-HIS [J].
CALLANT, D ;
COUSSENS, B ;
VANDERMATEN, T ;
DEVRIES, JG ;
DEVRIES, NK .
TETRAHEDRON-ASYMMETRY, 1992, 3 (03) :401-414
[6]   BINOLAM, a recoverable chiral ligand for bifunctional enantioselective catalysis:: The asymmetric synthesis of cyanohydrins [J].
Casas, J ;
Nájera, C ;
Sansano, JM ;
Saá, JM .
ORGANIC LETTERS, 2002, 4 (15) :2589-2592
[7]   Enantioselective cyanosilylation of ketones by a catalytic double-activation method with an aluminium complex and an N-oxide [J].
Chen, FX ;
Zhou, H ;
Liu, XH ;
Qin, B ;
Feng, XM ;
Zhang, GL ;
Jiang, YZ .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (19) :4790-4797
[8]   Synthesis of racemic tertiary cyanohydrins [J].
Chen, FX ;
Feng, XM .
SYNLETT, 2005, (06) :892-899
[9]   Enantioselective cyanosilylation of ketones by a catalytic double-activation method employing chiral Lewis acid and achiral N-oxide catalysts [J].
Chen, FX ;
Feng, XM ;
Qin, B ;
Zhang, GL ;
Jiang, YZ .
ORGANIC LETTERS, 2003, 5 (06) :949-952
[10]  
Chen FX, 2003, SYNLETT, P558