Co-Metal-Free Enantioselective Conjugate Addition Reactions of Zinc Reagents

被引:27
作者
Ay, Sefer [1 ]
Nieger, Martin [2 ]
Braese, Stefan [1 ]
机构
[1] Univ Karlsruhe, Inst Organ Chem, D-76131 Karlsruhe, Germany
[2] Univ Helsinki, Inorgan Chem Lab, FIN-00014 Helsinki, Finland
关键词
asymmetric catalysis; conjugate addition reactions; enals; N; O-ligands; organozinc reagents;
D O I
10.1002/chem.200801676
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric conjugate addition of diethylzine to cinnamaldehyde in a co-metal-free fashion by using N,O-ligands with planar and central chirality is described. Different modulations of the ligand structure, including several combinations of the chiral units. indicate that a [2.2]paracyclophane backbone is essential for the activity and the enantioselectivity of the generated active catalyst. By using the optimized ligand, an isolated yield of 90% was obtained with up to 99% ee.
引用
收藏
页码:11539 / 11556
页数:18
相关论文
共 117 条
[1]   CHIRAL HOMOENOLATE EQUIVALENTS .2. ASYMMETRIC-SYNTHESIS OF 3-SUBSTITUTED 3-PHENYLPROPIONALDEHYDES VIA METALLATED CHIRAL CINNAMYLAMINES [J].
AHLBRECHT, H ;
ENDERS, D ;
SANTOWSKI, L ;
ZIMMERMANN, G .
CHEMISCHE BERICHTE, 1989, 122 (10) :1995-2004
[2]   Highly enantioselective copper(I)-phosphoramidite-catalysed additions of organoaluminium reagents to enones [J].
Alexakis, A ;
Albrow, V ;
Biswas, K ;
d'Augustin, M ;
Prieto, O ;
Woodward, S .
CHEMICAL COMMUNICATIONS, 2005, (22) :2843-2845
[3]   Asymmetric conjugate addition to alkylidene malonates [J].
Alexakis, A ;
Benhaim, C .
TETRAHEDRON-ASYMMETRY, 2001, 12 (08) :1151-1157
[4]  
Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221
[5]   Enantioselective copper-catalyzed conjugate addition of dialkyl zinc to nitro-olefins [J].
Alexakis, A ;
Benhaim, C .
ORGANIC LETTERS, 2000, 2 (17) :2579-2581
[6]   Catalytic enantioselective synthesis of prostaglandin E1 methyl ester using a tandem 1,4-addition-aldol reaction to a cyclopenten-3,5-dione monoacetal [J].
Arnold, LA ;
Naasz, R ;
Minnaard, AJ ;
Feringa, BL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (24) :5841-5842
[7]   Recent applications of chiral ferrocene ligands in asymmetric catalysis [J].
Arrayas, Ramon Gomez ;
Adrio, Javier ;
Carretero, Juan Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) :7674-7715
[8]   α,β-unsaturated β-silyl imide substrates for catalytic, enantioselective conjugate additions:: A total synthesis of (+)-lactacystin and the discovery of a new proteasome inhibitor [J].
Balskus, Emily P. ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6810-6812
[9]  
Br?se, 2005, ANGEW CHEM, V117, P8091
[10]  
Brandau S., 2006, ANGEW CHEM, V118, P4411