Design and application of linked-BINOL chiral ligands in bifunctional asymmetric catalysis

被引：285

作者：

Shibasaki, M ^{[1
]}

Matsunaga, S ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

CHEMICAL SOCIETY REVIEWS | 2006年 / 35卷 / 03期

关键词：

D O I：

10.1039/b506346a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The design and application of linked-BINOLs investigated in our group are reviewed. Linked-BINOLs are a kind of semi-crown ether, thus they are flexible and applicable to metals having various ionic radii (Ga3+, Li+, Zn2+, In3+, La3+, and Y3+). The flexible linker segment, containing a coordinative heteroatom, has a crucial role in the construction of a unique and effective chiral environment that is not accessible from BINOL itself. Applications of linked-BINOLs to an epoxide opening reaction, Michael reactions, a direct aldol reaction, direct Michael reactions of a hydroxyketone, and direct Mannich-type reactions of hydroxyketones and N-acylpyrrole are described.

引用

页码：269 / 279

页数：11

共 38 条

[1]

Alcaide B, 2002, EUR J ORG CHEM, V2002, P1595

[2] The synthesis of vicinal amino alcohols [J].

Bergmeier, SC .

TETRAHEDRON, 2000, 56 (17) :2561-2576

[3] BINOL: A versatile chiral reagent [J].

Brunel, JM .

CHEMICAL REVIEWS, 2005, 105 (03) :857-897

[4] The direct catalytic asymmetric Mannich reaction [J].

Córdova, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) :102-112

[5] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[6] Stereoselective formation of quaternary carbon centers and related functions [J].

Denissova, I ;

Barriault, L .

TETRAHEDRON, 2003, 59 (51) :10105-10146

[7] Direct catalytic asymmetric Mannich-type reactions of N-(2-hydroxyacetyl)pyrrole as an ester-equivalent donor [J].

Harada, S ;

Handa, S ;

Matsunaga, S ;

Shibasaki, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (28) :4365-4368

[8] Direct catalytic asymmetric Michael reaction of hydroxyketones:: Asymmetric Zn catalysis with a Et2Zn/linked-BINOL complex [J].

Harada, S ;

Kumagai, N ;

Kinoshita, T ;

Matsunaga, S ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2582-2590

[9] HOST-GUEST COMPLEXATION .19. CYCLIC, BICYCLIC, AND TRICYCLIC POLYETHER SYSTEMS [J].

HELGESON, RC ;

TARNOWSKI, TL ;

CRAM, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) :2538-2550

[10] Chiral zirconium catalysts using multidentate BINOL derivatives for catalytic enantioselective Mannich-type reactions; Ligand optimization and approaches to elucidation of the catalyst structure [J].

Ihori, Y ;

Yamashita, Y ;

Ishitani, H ;

Kobayashi, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15528-15535

← 1 2 3 4 →