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
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
[1]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[2]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[3]  
[Anonymous], RSC ADV, DOI DOI 10.1039/C5RA17488K
[4]  
[Anonymous], 2013, ANGEW CHEM-GER EDIT
[5]   Development of a Formal Catalytic Asymmetric [4+2] Addition of Ethyl-2,3-butadienoate with Acyclic Enones [J].
Ashtekar, Kumar Dilip ;
Staples, Richard J. ;
Borhan, Babak .
ORGANIC LETTERS, 2011, 13 (21) :5732-5735
[6]   Metal-controlled selective [3+2] cyclization reactions of alkenyl Fischer carbene complexes and allenes [J].
Barluenga, J ;
Vicente, R ;
Barrio, P ;
López, LA ;
Tomás, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :5974-5975
[7]   Silver and Gold Catalysis for Cycloisomerization Reactions [J].
Belmont, Philippe ;
Parker, Evelyne .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (35) :6075-6089
[8]   Asymmetric Ion-Pairing Catalysis [J].
Brak, Katrien ;
Jacobsen, Eric N. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) :534-561
[9]   Enantioselective Intermolecular [2+2+2] Cycloadditions of Ene-Allenes with Allenoates [J].
Brusoe, Andrew T. ;
Edwankar, Rahul V. ;
Alexanian, Erik J. .
ORGANIC LETTERS, 2012, 14 (23) :6096-6099
[10]   Gold-Catalyzed Intramolecular [3+2] Cycloadditions of 1-Aryl-1-allene-6-enes [J].
Chaudhuri, Rupsha ;
Liao, Hsin-Yi ;
Liu, Rai-Shung .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (35) :8895-8901