Late-transition-metal complexes of BINOL-derived salens: Synthesis, structure, and reactivity

被引：48

作者：

DiMauro, EF ^{[1
]}

Kozlowski, MC ^{[1
]}

机构：

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

来源：

ORGANOMETALLICS | 2002年 / 21卷 / 07期

关键词：

D O I：

10.1021/om010571f

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Salen metal complexes incorporating two chiral BINOL moieties have been synthesized. From a comparison of the parent salen and the BINOL-salen X-ray crystal structures, the effect of the BINOL portions has been examined. In particular, the effects of intramolecular hydrogen bonding on the salen core structure have been determined. The bis(naphthoxide) complexes arising from deprotonation of the BINOL-salen metal complexes have been found to catalyze the asymmetric addition of benzyl malonate to cyclohexenone in up to 90% ee.

引用

页码：1454 / 1461

页数：8

共 35 条

[1] Immobilization of heterobimetallic multifunctional asymmetric catalyst [J].

Arai, T ;

Hu, QS ;

Zheng, XF ;

Pu, L ;

Sasai, H .

ORGANIC LETTERS, 2000, 2 (26) :4261-4263

[2] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[3] BINOL-salen metal catalysts incorporating a bifunctional design [J].

DiMauro, EF ;

Kozlowski, MC .

ORGANIC LETTERS, 2001, 3 (11) :1641-1644

[4] PREPARATION, SEPARATION, AND CHARACTERIZATION OF LEL3-ISOMERS AND OB3-ISOMERS OF TRIS(TRANS-1,2-CYCLOHEXANEDIAMINE) RHODIUM (III) COMPLEXES [J].

GALSBOL, F ;

STEENBOL, P ;

SORENSEN, BS .

ACTA CHEMICA SCANDINAVICA, 1972, 26 (09) :3605-3611

[5] A novel phosphinamide catalyst for the asymmetric reduction of ketones by borane [J].

Gamble, MP ;

Smith, ARC ;

Wills, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :6068-6071

[6] STRUCTURE OF ETA-3-ALLYL[1,2-BIS(DIMETHYLPHOSPHINO)ETHANE]-ETA-6-TOLUENETUNGSTEN HEXAFLUOROPHOSPHATE, [W(C3H5)(C7H8)(C6H16P2)]PF6 [J].

GOURDON, A ;

PROUT, K .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1983, 39 (JUL) :865-868

[7] Highly enantioselective cyanosilylation of aldehydes catalyzed by a Lewis acid-Lewis base bifunctional catalyst [J].

Hamashima, Y ;

Sawada, D ;

Nogami, H ;

Kanai, M ;

Shibasaki, M .

TETRAHEDRON, 2001, 57 (05) :805-814

[8] CATALYTIC ASYMMETRIC ALDOL REACTION - REACTION OF ALDEHYDES WITH ISOCYANOACETATE CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEX [J].

ITO, Y ;

SAWAMURA, M ;

HAYASHI, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6405-6406

[9]

Jacobsen E. N., 1999, COMPREHENSIVE ASYMME

[10] Catalytic enantioselective Michael addition reactions of alpha-nitroesters to alpha,beta-unsaturated ketones [J].

Keller, E ;

Veldman, N ;

Spek, AL ;

Feringa, BL .

TETRAHEDRON-ASYMMETRY, 1997, 8 (20) :3403-3413

← 1 2 3 4 →