A Direct Ylide Transfer to Carbonyl Derivatives and Heteroaromatic Compounds

被引：46
作者：
Huang, Xueliang [1 ]
Goddard, Richard [1 ]
Maulide, Nuno [1 ]
机构：
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 47期
关键词：
rearrangement; structure elucidation; sulfuranes; transfer reactions; ylides; STABILIZED SULFONIUM YLIDES; STABLE SULFUR YLIDES; IN-SITU GENERATION; ACTIVE METHYLENE-COMPOUNDS; ASYMMETRIC-SYNTHESIS; DIAZO-COMPOUNDS; DIMETHYLSULFONIUM METHYLIDE; STEREOSELECTIVE-SYNTHESIS; CONVENIENT SYNTHESIS; CHIRAL SULFIDES;
D O I：
10.1002/anie.201002919
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Power transfer: The title reaction proceeds under mild conditions (room temperature, short reaction times) and directly affords sulfonium ylides from active methylene compounds and heteroaromatics in a single step and in high yields. A detailed comparative structural analysis of a variety of ylides is presented and the implications of structure on the reactivity of these compounds are discussed. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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页码：8979 / 8983
页数：5
相关论文
共 105 条
[1]  
Aggarwal V.K., 2001, ANGEW CHEM, V113, P1482
[2]  
Aggarwal V.K., 2001, Angew. Chem, V113, P1479
[3]   Asymmetric sulfonium ylide mediated cyclopropanation: Stereocontrolled synthesis of (+)-LY354740 [J].
Aggarwal, VK ;
Grange, E .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (02) :568-575
[4]   Highly enantioselective synthesis of glycidic amides using camphor-derived sulfonium salts. Mechanism and applications in synthesis [J].
Aggarwal, VK ;
Charmant, JPH ;
Fuentes, D ;
Harvey, JN ;
Hynd, G ;
Ohara, D ;
Picoul, W ;
Robiette, R ;
Vasse, JL ;
Winn, CL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) :2105-2114
[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]  
Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1430, DOI 10.1002/1521-3773(20010417)40:8<1430::AID-ANIE1430>3.0.CO
[8]  
2-W
[9]  
Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO
[10]  
2-E
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