trans-1,2-diaminocyclopentane-based catalyst for the asymmetric addition of alkyl-, aryl-, and vinyl groups to ketones

被引：32

作者：

de Parrodi, CA

Walsh, PJ ^{[1
]}

机构：

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

[2] Univ Americas Puebla, Dept Quim & Biol, Cholula 72820, Mexico

来源：

SYNLETT | 2004年 / 13期

关键词：

alcohols; asymmetric catalysis; ketones; quaternary centers; ligands;

D O I：

10.1055/s-2004-832826

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic asymmetric addition of ethyl-, phenyl-, and 1-hexenyl groups to ketones is reported. The new catalyst, generated from titanium isopropoxide and a bis(sulfonamide) diol ligand based on trans-1,2-diaminocyclopentane, gives good to excellent enantioselectivities with a range of substrates.

引用

收藏

页码：2417 / 2420

页数：4

相关论文

共 16 条

[1] Development of the first practical catalyst for the asymmetric addition of alkyl- and arylzinc reagents to ketones [J].

Betancort, JM ;

García, C ;

Walsh, PJ .

SYNLETT, 2004, (05) :749-760

[2]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO

[3]

2-V

[4] Development of bifunctional salen catalysts:: Rapid, chemoselective alkylations of α-ketoesters [J].

DiMauro, EF ;

Kozlowski, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12668-12669

[5] Catalytic asymmetric addition of ZnPh2 to ketones:: Enantioselective formation of quaternary stereocenters [J].

Dosa, PI ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :445-446

[6]

Eliel E.L., 1994, Stereochemistry of Organic Compounds

[7] Multicenter strategy for the development of catalytic enantioselective nucleophilic alkylation of ketones:: Me2Zn addition to α-ketoesters [J].

Funabashi, K ;

Jachmann, M ;

Kanai, M ;

Shibasaki, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5489-5492

[8] A practical catalytic asymmetric addition of alkyl groups to ketones [J].

García, C ;

LaRochelle, LK ;

Walsh, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (37) :10970-10971

[9] Highly enantioselective catalytic phenylation of ketones with a constrained geometry titanium catalyst [J].

García, C ;

Walsh, PJ .

ORGANIC LETTERS, 2003, 5 (20) :3641-3644

[10] Asymmetric addition of alkylzinc reagents to cyclic α,β-unsaturated ketones and a tandem enantioselective addition/diastereoselective epoxidation with dioxygen [J].

Jeon, SJ ;

Walsh, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9544-9545