Catalytic Regio- and Enantioselective [4+2] Annulation Reactions of Non-activated Allenes by a Chiral Cationic Indium Complex

被引：46
作者：
Wang, Le [1 ,2 ]
Lv, Jian [1 ,2 ,3 ]
Zhang, Long [1 ,2 ,3 ]
Luo, Sanzhong [1 ,2 ,3 ]
机构：
[1] Chinese Acad Sci, Inst Chem, Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 36期
关键词：
4+2] annulation; allenes; chiral phosphates; homogeneous catalysis; indium; ASYMMETRIC BINARY-ACID; DIELS-ALDER REACTION; BRONSTED ACID; PHOSPHINE CATALYSIS; PHOSPHORIC-ACID; SIMPLE OLEFINS; CYCLOADDITIONS; ALLENOATES; METAL; CYCLIZATION;
D O I：
10.1002/anie.201704020
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Regio- and enantioselective [4+2] annulation between beta,gamma-unsaturated alpha-keto esters and non-activated allenes was achieved by using a chiral cationic indium(III)/phosphate catalyst. The reaction affords the corresponding C3-selective dihydropyrans in good yields and with high enantioselectivity (up to 99% ee).
引用
收藏
页码：10867 / 10871
页数：5
相关论文
共 84 条
[21]   Gold-Catalyzed Nucleophilic Cyclization of Functionalized Allenes: A Powerful Access to Carbo- and Heterocycles [J].
Krause, Norbert ;
Winter, Christian .
CHEMICAL REVIEWS, 2011, 111 (03) :1994-2009
[22]   Enantioselective Synthesis of Spirobarbiturate-Cyclohexenes through Phosphine-Catalyzed Asymmetric [4+2] Annulation of Barbiturate-Derived Alkenes with Allenoates [J].
Liu, Honglei ;
Liu, Yang ;
Yuan, Chunhao ;
Wang, Guo-Peng ;
Zhu, Shou-Fei ;
Wu, Yang ;
Wang, Bo ;
Sun, Zhanhu ;
Xiao, Yumei ;
Zhou, Qi-Lin ;
Guo, Hongchao .
ORGANIC LETTERS, 2016, 18 (06) :1302-1305
[23]   Characterization of the switch in the mechanism of an intramolecular Diels-Alder reaction [J].
Lopez, Carlos Silva ;
Faza, Olalla Nieto ;
de Lera, Angel R. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (02) :467-473
[24]   Reactions of electron-deficient alkynes and allenes under phosphine catalysis [J].
Lu, XY ;
Zhang, CM ;
Xu, ZR .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (07) :535-544
[25]  
Lv J., 2013, ANGEW CHEM, V125, P9968
[26]  
Lv J, 2011, Angew. Chem., V123, P6740
[27]  
Lv J., 2014, ACTA CHIM SINICA, V72, P809
[28]   Asymmetric Latent Carbocation Catalysis with Chiral Trityl Phosphate [J].
Lv, Jian ;
Zhang, Qichao ;
Zhong, Xingren ;
Luo, Sanzhong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (49) :15576-15583
[29]   Taming Living Carbocations in Catalytic Direct Conjugate Addition of Simple Alkenes to α,β-Enones [J].
Lv, Jian ;
Zhong, Xingren ;
Luo, Sanzhong .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (27) :8293-8296
[30]   Switchable Diastereoselectivity in Enantioselective [4+2] Cycloadditions with Simple Olefins by Asymmetric Binary Acid Catalysis [J].
Lv, Jian ;
Zhang, Long ;
Luo, Sanzhong ;
Cheng, Jin-Pei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) :9786-9790
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