Catalytic and asymmetric vinylogous mukaiyama reactions on aliphatic ketones:: Formal asymmetric synthesis of taurospongin A

被引：74

作者：

Moreau, X ^{[1
]}

Bazán-Tejeda, B ^{[1
]}

Campagne, JM ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 20期

关键词：

D O I：

10.1021/ja051573k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic asymmetric vinylogous Mukaiyama reactions on ketones, leading to the formation of α,β-unsaturated lactones with tertiary alcohols, have been described (11 examples, up to 93% ee). This methodology has been applied in a formal enantioselective synthesis of taurospongin A (12 steps, 6% overall yield). Copyright © 2005 American Chemical Society.

引用

页码：7288 / 7289

页数：2

共 46 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] Catalytic asymmetric access to α,β unsaturated δ-lactones through a vinylogous aldol reaction:: Application to the total synthesis of the Prelog-Djerassi lactone [J].

Bluet, G ;

Bazán-Tejeda, B ;

Campagne, JM .

ORGANIC LETTERS, 2001, 3 (23) :3807-3810

[3] Catalytic Asymmetric Vinylogous Mukaiyama-aldol (CAVM) reactions: The enolate activation [J].

Bluet, G ;

Campagne, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4293-4298

[4] Catalytic asymmetric vinylogous Mukaiyama (CAVM) reactions: aldehyde activation versus enolate activation [J].

Bluet, G ;

Campagne, JM .

TETRAHEDRON LETTERS, 1999, 40 (30) :5507-5509

[5] BINOL-Ti-catalyzed synthesis of tertiary homoallylic alcohols: The first catalytic asymmetric allylation of ketones [J].

Casolari, S ;

D'Addario, D ;

Tagliavini, E .

ORGANIC LETTERS, 1999, 1 (07) :1061-1063

[6] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions [J].

Christoffers, J ;

Baro, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1688-1690

[7]

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

[8]

2-V

[9] Enantioselective alkynylation of ketones catalyzed by Zn(salen) complexes [J].

Cozzi, PG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (25) :2895-2898

[10] On the use of mixtures of organotin species for catalytic enantioselective ketone allylation - a detective story [J].

Cunningham, A ;

Mokal-Parekh, V ;

Wilson, C ;

Woodward, S .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (05) :741-748

← 1 2 3 4 5 →