Reactions of iminium ions with Michael acceptors through a Morita-Baylis-Hillman-type reaction: Enantiocontrol and applications in synthesis

被引：73

作者：

Myers, Eddie L.

de Vries, Johannes G.

Aggarwal, Varinder K.

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] DSM Pharmaceut Prod, Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 11期

关键词：

C-C coupling; Lewis acids; Lewis bases; Mannich reaction; Morita-Baylis-Hillman reaction; IN-SITU GENERATION; ALPHA-ALKOXYALKYLATION; RADICAL CYCLIZATIONS; CARBONYL-COMPOUNDS; ALKALOID SYNTHESIS; ALDOL REACTION; ENONES; (+)-HELIOTRIDINE; EFFICIENT; SCOPE;

D O I：

10.1002/anie.200604715

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) All adducts one way: Iminium ions, generated in situ from the corresponding N,O-acetals, can be used as electrophiles in a Morita-Baylis-Hillman-type reaction with a wide range of Michael acceptors (enones, enals, S- and O-acrylates). The reaction has been rendered asymmetric using sulfide 1 (see scheme; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene, TMSOTf=trimethylsilyl trifluoromethanesulfonate). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：1893 / 1896

页数：4

相关论文

共 59 条

[1]

Aggarwal V.K., 2003, ANGEW CHEM, V115, P3396

[2]

Aggarwal V.K., 2001, Angew. Chem, V113, P1479

[3] A practical synthesis of a [2.2.1] bicyclic chiral sulfide for asymmetric transformations [J].

Aggarwal, Varinder K. ;

Fang, Guangyu ;

Kokotos, Christoforos G. ;

Richardson, Jeffery ;

Unthank, Matthew G. .

TETRAHEDRON, 2006, 62 (49) :11297-11303

[4] On the importance of leaving group ability in reactions of ammonium, oxonium, phosphonium, and sulfonium ylides [J].

Aggarwal, VK ;

Harvey, JN ;

Robiette, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5468-5471

[5] Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].

Aggarwal, VK ;

Winn, CL .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620

[6] A new protocol for the in situ generation of aromatic, heteroaromatic, and unsaturated diazo compounds and its application in catalytic and asymmetric epoxidation of carbonyl compounds. Extensive studies to map out scope and limitations, and rationalization of diastereo- and enantioselectivities [J].

Aggarwal, VK ;

Alonso, E ;

Bae, I ;

Hynd, G ;

Lydon, KM ;

Palmer, MJ ;

Patel, M ;

Porcelloni, M ;

Richardson, J ;

Stenson, RA ;

Studley, JR ;

Vasse, JL ;

Winn, CL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10926-10940

[7] Sulfur-ylide-mediated synthesis of functionalized and trisubstituted epoxides with high enantioselectivity; Application to the synthesis of CDP-840 [J].

Aggarwal, VK ;

Bae, I ;

Lee, HY ;

Richardson, J ;

Williams, DT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (28) :3274-3278

[8] Correlation between pKa and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction:: Discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope [J].

Aggarwal, VK ;

Emme, I ;

Fulford, SY .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :692-700

[9]

Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1430, DOI 10.1002/1521-3773(20010417)40:8<1430::AID-ANIE1430>3.0.CO

[10]

2-W

← 1 2 3 4 5 6 →