Indium-mediated asymmetric allylation of acylhydrazones using a chiral urea catalyst

被引：139

作者：

Tan, Kian L. ^{[1
]}

Jacobsen, Eric N. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 08期

关键词：

allylation; asymmetric catalysis; indium; synthetic methods;

D O I：

10.1002/anie.200603354

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Urea-ka! A new role for urea-based chiral catalysts has been uncovered in the asymmetric allylation of acylhydrazones with allylindium reagents (see scheme; Bz: benzoyl). The best results were obtained using the bifunctional catalyst 1, which bears a Lewis basic sulfanamide. This example represents the first highly enantioselective addition of an organometallic reagent catalyzed by a chiral urea catalyst. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1315 / 1317

页数：3

共 43 条

[1]

Alvaro G, 2002, SYNLETT, P651

[2]

[Anonymous], 2006, ANGEW CHEM, V118, P1550

[3] Enantioselective allylation of ketone-derived benzoylhydrazones: Practical synthesis of tertiary carbinarnines [J].

Berger, R ;

Duff, K ;

Leighton, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5686-5687

[4] Toward a versatile allylation reagent: Practical, enantioselective allylation of acylhydrazones using strained silacycles [J].

Berger, R ;

Rabbat, PMA ;

Leighton, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9596-9597

[5] Organocatalysis mediated by (thio)urea derivatives [J].

Connon, Stephen J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5418-5427

[6] Catalytic enantioselective indium-mediated allylation of hydrazones [J].

Cook, GR ;

Kargbo, R ;

Maity, B .

ORGANIC LETTERS, 2005, 7 (13) :2767-2770

[7] Highly diastereoselective indium-mediated allylation of chiral hydrazones [J].

Cook, GR ;

Maity, BC ;

Kargbo, R .

ORGANIC LETTERS, 2004, 6 (11) :1741-1743

[8] Diastereo- and regioselective palladium-indium bimetallic cyclisation-Barbier-type allylation cascades [J].

Cooper, IR ;

Grigg, R ;

MacLachlan, WS ;

Sridharan, V ;

Thornton-Pett, M .

TETRAHEDRON LETTERS, 2003, 44 (02) :403-405

[9] 3-Component palladium-indium mediated diastereoselective cascade allylation of imines with allenes and aryl iodides [J].

Cooper, IR ;

Grigg, R ;

MacLachlan, WS ;

Thornton-Pett, M ;

Sridharan, V .

CHEMICAL COMMUNICATIONS, 2002, (13) :1372-1373

[10] Asymmetric addition of allylic nucleophiles to imino compounds [J].

Ding, H ;

Friestad, GK .

SYNTHESIS-STUTTGART, 2005, (17) :2815-2829

← 1 2 3 4 5 →