Nickel complexes from α-amino amides as efficient catalysts for the enantioselective Et2Zn addition to benzaldehyde

被引:43
作者
Burguete, MI [1 ]
Collado, M [1 ]
Escorihuela, J [1 ]
Galindo, F [1 ]
García-Verdugo, E [1 ]
Luis, SV [1 ]
Vicent, MJ [1 ]
机构
[1] Univ Jaume 1, Dept Inorgan & Organ Chem, ESTCE, E-12080 Castellon de La Plana, Spain
关键词
D O I
10.1016/S0040-4039(03)01705-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ni2+ complexes derived from simple alpha-amino amides catalyze very efficiently the addition of Et2Zn to benzaldehyde, giving (S)-1-phenylethanol as the major isomer in most cases (94% yield, 97% ee for R=Bn). The nature of the substituent on the amide nitrogen atom seems to play a key role in determining the asymmetric induction observed. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6891 / 6894
页数:4
相关论文
共 58 条
[1]  
Adrián F, 1999, EUR J INORG CHEM, P2347
[2]   Enantioselective addition of dialkylzinc to aldehydes catalyzed by (S)-2-(N,N-disubstituted aminomethyl)indoline [J].
Asami, M ;
Watanabe, H ;
Honda, K ;
Inoue, S .
TETRAHEDRON-ASYMMETRY, 1998, 9 (23) :4165-4173
[3]   Enantioselective addition of diethylzinc to aldehydes catalyzed by (S)-2-(N,N-disubstituted aminomethyl)pyrrolidine [J].
Asami, M ;
Inoue, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (07) :1687-1690
[4]   New supported β-amino alcohols as efficient catalysts for the enantioselective addition of diethylzinc to benzaldehyde under flow conditions [J].
Burguete, MI ;
García-Verdugo, E ;
Vicent, MJ ;
Luis, SV ;
Pennemann, H ;
von Keyserling, NG ;
Martens, J .
ORGANIC LETTERS, 2002, 4 (22) :3947-3950
[5]   Development of small focused libraries of supported amino alcohols as an efficient strategy for the optimization of enantioselective heterogeneous catalysts for the ZnEt2 addition to benzaldehyde [J].
Burguete, MI ;
Collado, M ;
García-Verdugo, E ;
Vicent, MJ ;
Luis, SV ;
von Keyserling, NG ;
Martens, J .
TETRAHEDRON, 2003, 59 (10) :1797-1804
[6]   SYNTHESIS AND CHARACTERIZATION OF NEW CHIRAL RH(I) COMPLEXES WITH N,N'-LIGANDS AND N,P-LIGANDS - A STUDY OF ANCHORING ON THE MODIFIED ZEOLITES AND CATALYTIC PROPERTIES OF HETEROGENIZED COMPLEXES [J].
CARMONA, A ;
CORMA, A ;
IGLESIAS, M ;
SANJOSE, A ;
SANCHEZ, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 492 (01) :11-21
[7]   X-RAY CRYSTALLOGRAPHIC AND NMR-STUDIES ON THE ORIGINS OF HIGH ENANTIOSELECTIVITY IN DIELS-ALDER REACTIONS CATALYZED BY A CHIRAL DIAZAALUMINOLIDINE [J].
COREY, EJ ;
SARSHAR, S ;
BORDNER, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) :7938-7939
[8]   CONJUGATE ADDITION OF DIETHYLZINC TO ENONES CATALYZED BY HOMOGENEOUS AND SUPPORTED CHIRAL NI-COMPLEXES - COOPERATIVE EFFECT OF THE SUPPORT ON ENANTIOSELECTIVITY [J].
CORMA, A ;
IGLESIAS, M ;
MARTIN, MV ;
RUBIO, J ;
SANCHEZ, F .
TETRAHEDRON-ASYMMETRY, 1992, 3 (07) :845-848
[9]   Heterogenised catalysts on zeolites. Synthesis of new chiral Rh(I) complexes with (2S,4R)-trans-4-RCOO-2-(t-butylaminocarbonyl)pyrrolidines and (2S,4S)-cis-4-RCONH-2-(t-butylaminocarbonyl)pyrrolidines. Heterogenisation on silica and a USY-zeolite and study of the role of support on their catalytic profile in hydrogenation of olefins [J].
Corma, A ;
Iglesias, M ;
Mohino, F ;
Sanchez, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 544 (02) :147-156
[10]   OPTICALLY-ACTIVE COMPLEXES OF TRANSITION-METALS (RH(I), RU(II), CO(II) AND NI(II)) WITH 2-AMINOCARBONYLPYRROLIDINE LIGANDS - SELECTIVE CATALYSTS FOR HYDROGENATION OF PROCHIRAL OLEFINS [J].
CORMA, A ;
IGLESIAS, M ;
DELPINO, C ;
SANCHEZ, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 431 (02) :233-246