Highly enantioselective catalytic carbon dioxide incorporation reaction: Nickel-catalyzed asymmetric carboxylative cyclization of bis-1,3-dienes

被引:176
作者
Takimoto, M [1 ]
Nakamura, Y [1 ]
Kimura, K [1 ]
Mori, M [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
关键词
D O I
10.1021/ja049506y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A method for nickel-catalyzed asymmetric carbon dioxide (CO2) incorporation via carbon-carbon bond formation was developed. In the presence of a catalytic amount of Ni(acac)2 and MeO-MOP, various bis-1,3-dienes reacted with CO2 (1 atm) and a diorganozinc reagent (Me2Zn or Ph2Zn) to afford cyclic carboxylic acids in good yields (71-100%) and with high enantioselectivities (90-96% ee). Copyright © 2003 American Chemical Society.
引用
收藏
页码:5956 / 5957
页数:2
相关论文
共 20 条
[1]   Catalysis research of relevance to carbon management: Progress, challenges, and opportunities [J].
Arakawa, H ;
Aresta, M ;
Armor, JN ;
Barteau, MA ;
Beckman, EJ ;
Bell, AT ;
Bercaw, JE ;
Creutz, C ;
Dinjus, E ;
Dixon, DA ;
Domen, K ;
DuBois, DL ;
Eckert, J ;
Fujita, E ;
Gibson, DH ;
Goddard, WA ;
Goodman, DW ;
Keller, J ;
Kubas, GJ ;
Kung, HH ;
Lyons, JE ;
Manzer, LE ;
Marks, TJ ;
Morokuma, K ;
Nicholas, KM ;
Periana, R ;
Que, L ;
Rostrup-Nielson, J ;
Sachtler, WMH ;
Schmidt, LD ;
Sen, A ;
Somorjai, GA ;
Stair, PC ;
Stults, BR ;
Tumas, W .
CHEMICAL REVIEWS, 2001, 101 (04) :953-996
[2]   CARBON-DIOXIDE AS AN ALTERNATIVE C1 SYNTHETIC UNIT - ACTIVATION BY TRANSITION-METAL COMPLEXES [J].
BEHR, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (05) :661-678
[3]   REACTIONS OF CARBON-DIOXIDE WITH CARBON CARBON BOND FORMATION CATALYZED BY TRANSITION-METAL COMPLEXES [J].
BRAUNSTEIN, P ;
MATT, D ;
NOBEL, D .
CHEMICAL REVIEWS, 1988, 88 (05) :747-764
[4]   Enantiomerically-enriched organic reagents via polymer synthesis:: enantioselective copolymerization of cycloalkene oxides and CO2 using homogeneous, zinc-based catalysts [J].
Cheng, M ;
Darling, NA ;
Lobkovsky, EB ;
Coates, GW .
CHEMICAL COMMUNICATIONS, 2000, (20) :2007-2008
[5]   Chiral monodentate phosphine ligand MOP for transition metal-catalyzed asymmetric reactions [J].
Hayashi, T .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :354-362
[7]   Efficient nickel-catalyzed [2+2+2] cycloaddition of CO2 and diynes [J].
Louie, J ;
Gibby, JE ;
Farnworth, MV ;
Tekavec, TN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) :15188-15189
[8]   NEW CHIRAL ANISOTROPIC REAGENTS FOR DETERMINING THE ABSOLUTE-CONFIGURATION OF CARBOXYLIC-ACIDS [J].
NAGAI, Y ;
KUSUMI, T .
TETRAHEDRON LETTERS, 1995, 36 (11) :1853-1856
[9]   Asymmetric alternating copolymerization of cyclohexene oxide and CO2 with dimeric zinc complexes [J].
Nakano, K ;
Nozaki, K ;
Hiyama, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (18) :5501-5510
[10]   Optically active polycarbonates: Asymmetric alternating copolymerization of cyclohexene oxide and carbon dioxide [J].
Nozaki, K ;
Nakano, K ;
Hiyama, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (47) :11008-11009