Organocatalytic enantioselective nucleophilic vinylic substitution

被引：102

作者：

Poulsen, Thomas B. ^{[1
]}

Bernardi, Luca ^{[1
]}

Bell, Mark ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 39期

关键词：

addition-elimination; asymmetric synthesis; organocatalysis; phase-transfer catalysis; vinylation;

D O I：

10.1002/anie.200602275

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) The clash of hybridizations: A tailored phase-transfer organocatalyst merges sp3-and sp2- hybridized carbon atoms by catalyzing the first enantioselective vinylic substitution (see scheme; EWG = electron-withdrawing group). The method provides access to optically active compounds possessing vinyl-substituted quaternary stereocenters with control of the alkene configuration. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6551 / 6554

页数：4

共 39 条

[1] Organocatalytic regio- and asymmetric C-selective SNAr reactions-stereoselective synthesis of optically active spiro-pyrrolidone-3,3′-oxoindoles [J].

Bella, M ;

Kobbelgaard, S ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) :3670-3671

[2] Organocatalytic enantioselective conjugate addition to alkynones [J].

Bella, M ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5672-5673

[3] Catalytic asymmetric vinylation of ketone enolates [J].

Chieffi, A ;

Kamikawa, K ;

Åhman, J ;

Fox, JM ;

Buchwald, SL .

ORGANIC LETTERS, 2001, 3 (12) :1897-1900

[4] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].

Corey, EJ ;

Xu, F ;

Noe, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415

[5] Catalytic enantioselective Conia-ene reaction [J].

Corkey, BK ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17168-17169

[6]

Dalko P.I., 2004, ANGEW CHEM, V116, P5248, DOI DOI 10.1002/ANGE.200400650

[7]

Dalko P. I., 2001, ANGEW CHEM-GER EDIT, V113, P3840

[8]

Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO

[9]

2-D

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

Dalko, PI ;

Moisan, L .

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

← 1 2 3 4 →