BINOL-salen metal catalysts incorporating a bifunctional design

被引：73

作者：

DiMauro, EF ^{[1
]}

Kozlowski, MC ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 11期

关键词：

D O I：

10.1021/ol0158213

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Salen metal complexes Incorporating two chiral BINOL moieties have been synthesized and characterized crystallographically. The corresponding bisnaphthoxide complexes have been found to catalyze the asymmetric addition of benzyl malonate to cyclohexenone in up to 90% ee. With these modular catalysts, the Lewis acid and Bronsted base portions can be independently altered.

引用

页码：1641 / 1644

页数：4

共 25 条

[1] Immobilization of heterobimetallic multifunctional asymmetric catalyst
Arai, T
Hu, QS
Zheng, XF
Pu, L
Sasai, H
[J]. ORGANIC LETTERS, 2000, 2 (26) : 4261 - 4263
[2] The use of achiral ligands to convey asymmetry: Chiral environment amplification
Balsells, J
Walsh, PJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) : 1802 - 1803
[3] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS
COREY, EJ
BAKSHI, RK
SHIBATA, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) : 5551 - 5553
[4] A novel phosphinamide catalyst for the asymmetric reduction of ketones by borane
Gamble, MP
Smith, ARC
Wills, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) : 6068 - 6071
[5] Highly enantioselective cyanosilylation of aldehydes catalyzed by a Lewis acid-Lewis base bifunctional catalyst
Hamashima, Y
Sawada, D
Nogami, H
Kanai, M
Shibasaki, M
[J]. TETRAHEDRON, 2001, 57 (05) : 805 - 814
[6] CATALYTIC ASYMMETRIC ALDOL REACTION - REACTION OF ALDEHYDES WITH ISOCYANOACETATE CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEX
ITO, Y
SAWAMURA, M
HAYASHI, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) : 6405 - 6406
[7] Jacobsen E. N., 1999, COMPREHENSIVE ASYMME
[8] Catalytic enantioselective Michael addition reactions of alpha-nitroesters to alpha,beta-unsaturated ketones
Keller, E
Veldman, N
Spek, AL
Feringa, BL
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (20) : 3403 - 3413
[9] Stable, storable, and reusable asymmetric catalyst: A novel La-linked-BINOL complex for the catalytic asymmetric Michael reaction
Kim, YS
Matsunaga, S
Das, J
Sekine, A
Ohshima, T
Shibasaki, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) : 6506 - 6507
[10] N,N,N',N'-tetraalkyl-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxamides: Novel chiral auxiliaries for asymmetric Simmons-Smith cyclopropanation of allylic alcohols and for asymmetric diethylzinc addition to aldehydes
Kitajima, H
Ito, K
Aoki, Y
Katsuki, T
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (01) : 207 - 217

← 1 2 3 →