Construction of Optically Active Indolines by Formal [4+1] Annulation of Sulfur Ylides and N-(ortho-Chloromethyl)aryl Amides

被引:96
作者
Yang, Qing-Qing [1 ]
Wang, Qiang [1 ]
An, Jing [1 ]
Chen, Jia-Rong [1 ]
Lu, Liang-Qiu [1 ]
Xiao, Wen-Jing [1 ]
机构
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
基金
美国国家科学基金会;
关键词
annulation; asymmetric synthesis; cascade reaction; indolines; sulfur ylides; CATALYZED ASYMMETRIC HYDROGENATION; HIGHLY ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CASCADE REACTIONS; HETEROCYCLIC ARCHITECTURES; ALKENE HYDROAMINATION; CARBONYL-COMPOUNDS; SULFOXONIUM YLIDE; MICHAEL ADDITION; TANDEM REACTIONS;
D O I
10.1002/chem.201300988
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Get asymmetric! Asymmetric [4+1] annulation of sulfur ylides and N-(ortho-chloromethyl)aryl amides allowed the formation of the desired cycloadduct with moderate to high yields and enantioselectivities (see scheme). The described strategy, taking advantage of chiral sulfur ylides, represents a direct procedure to access chiral 2-substituted indolines. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:8401 / 8404
页数:4
相关论文
共 103 条
[1]  
Aggarwal V. K., 2003, ANGEW CHEM, V115, P3396
[2]   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
[3]   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
[4]   Effect of sulfide structure on enantioselectivity in catalytic asymmetric epoxidation of aldehydes: Mechanistic insights and implications [J].
Aggarwal, VK ;
Charmant, J ;
Dudin, L ;
Porcelloni, M ;
Richardson, J .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5467-5471
[5]   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
[6]   Unraveling the mechanism of epoxide formation from sulfur ylides and aldehydes [J].
Aggarwal, VK ;
Harvey, JN ;
Richardson, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) :5747-5756
[7]   New chiral lanthanide amide ate complexes for the catalysed synthesis of scalemic nitrogen-containing heterocycles [J].
Aillaud, Isabelle ;
Collin, Jacqueline ;
Duhayon, Carine ;
Guillot, Regis ;
Lyubov, Dmitrii ;
Schulz, Emmanuelle ;
Trifonov, Alexander .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (07) :2189-2200
[8]   Enantioselective Construction of Oxa- and Aza-Angular Triquinanes through Tandem [4+1]/[3+2] Cycloaddition of Sulfur Ylides and Nitroolefins [J].
An, Jing ;
Lu, Liang-Qiu ;
Yang, Qing-Qing ;
Wang, Tao ;
Xiao, Wen-Jing .
ORGANIC LETTERS, 2013, 15 (03) :542-545
[9]   Routes toward enantiopure 2-substituted indolines: an overview [J].
Anas, Saithalavi ;
Kagan, Henri B. .
TETRAHEDRON-ASYMMETRY, 2009, 20 (19) :2193-2199
[10]   Synthesis of two (S)-indoline-based chiral auxiliaries and their use in diastereoselective alkylation reactions [J].
Andersson, Fredrik ;
Hedenstrom, Erik .
TETRAHEDRON-ASYMMETRY, 2006, 17 (13) :1952-1957