Highly enantioselective Aza-Baylis-Hillman reaction in a chiral reaction medium

被引:160
作者
Gausepohl, Rolf
Buskens, Pascal
Kleinen, Jochen
Bruckmann, Angelika
Lehmann, Christian W.
Klankermayer, Jurgen
Leitner, Walter
机构
[1] Rhein Westfal TH Aachen Klinikum, Inst Tech & Makromol Chem, D-52074 Aachen, Germany
[2] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
asymmetric synthesis; C-C coupling; chiral solvents; ionic liquids; organocatalysis;
D O I
10.1002/anie.200600327
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Let's twist again! The first highly enantioselective asymmetric reaction in which a chiral reaction medium is the sole source of chirality is presented. The aza-Baylis-Hillman reaction in an ionic liquid with a chiral anion, whose design is based on mechanistic insights, gave products with up to M% ee. (Figure Presented). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3689 / 3692
页数:4
相关论文
共 29 条
[1]  
[Anonymous], ANGEW CHEM
[2]   Chiral quinuclidine-based amine catalysts for the asymmetric one-pot, three-component aza-Baylis-Hillman reaction [J].
Balan, D ;
Adolfsson, H .
TETRAHEDRON LETTERS, 2003, 44 (12) :2521-2524
[3]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[4]   Chiral ionic liquids, a renewal for the chemistry of chiral solvents?: Design, synthesis and applications for chiral recognition and asymmetric synthesis [J].
Baudequin, C ;
Brégeon, D ;
Levillain, J ;
Guillen, F ;
Plaquevent, JC ;
Gaumont, AC .
TETRAHEDRON-ASYMMETRY, 2005, 16 (24) :3921-3945
[5]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[6]  
Boeseken J, 1925, RECL TRAV CHIM PAY-B, V44, P758
[7]   Bifunctional activation and racemization in the catalytic asymmetric aza-Baylis-Hillman reaction [J].
Buskens, P ;
Klankermayer, J ;
Leitner, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (48) :16762-16763
[8]  
CUNNINGHAM PH, 1996, Patent No. 95109113
[9]   Chiral ionic liquids: Synthesis and applications [J].
Ding, J ;
Armstrong, DW .
CHIRALITY, 2005, 17 (05) :281-292
[10]   Use of chiral ionic liquids as solvents for the enantioselective photoisomerization of dibenzobicyclo[2.2.2]octatrienes [J].
Ding, J ;
Desikan, V ;
Han, XX ;
Xiao, TL ;
Ding, RF ;
Jenks, WS ;
Armstrong, DW .
ORGANIC LETTERS, 2005, 7 (02) :335-337