Phosphine-mediated enantioselective synthesis of carbocycles and heterocycles

被引:39
作者
Gao, Yu-Ning [1 ]
Shi, Min [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
Bifunctional phosphines; Asymmetric catalysis; Carbocycles; Heterocycles; Cycloaddition reactions; BAYLIS-HILLMAN CARBONATES; N-SULFONATED IMINES; ASYMMETRIC 3+2 ANNULATION; CATALYZED 4+2 ANNULATION; C; N-CYCLIC AZOMETHINE IMINES; ELECTRON-DEFICIENT OLEFINS; METHYL VINYL KETONE; CHIRAL-PHOSPHINE; DIASTEREOSELECTIVE CONSTRUCTION; ALLYLIC SUBSTITUTION;
D O I
10.1016/j.cclet.2016.12.001
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Nucleophilic chiral phosphine catalysis has been prosperous in asymmetric synthesis over the past two decades. Various tunable chiral phosphines display excellent activity and selectivity in asymmetric transformations including acycloaddition reactions and cycloaddition reactions. Enantiomerically enriched cyclic compounds are ubiquitous in natural products and drug molecules. These phosphinecatalyzed reactions provide effective and extensive strategies for the synthesis of a series of complex cyclic compounds as well as the synthesis of chiral compounds which could be easily transformed to carbocycles and heterocycles. This minireview summarizes recent developments in this area and highlights meaningful breakthroughs. (C) 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:493 / 502
页数:10
相关论文
共 114 条
[1]  
[Anonymous], 2010, CATALYTIC ASYMMETRIC
[2]   The Baylis-Hillman reaction: a novel concept for creativity in chemistry [J].
Basavaiah, Deevi ;
Veeraraghavaiah, Gorre .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (01) :68-78
[3]   Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].
Basavaiah, Deevi ;
Reddy, Bhavanam Sekhara ;
Badsara, Satpal Singh .
CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674
[4]  
Baylis A. B., 1972, German Pat, Patent No. 2155113
[5]   Catalytic Asymmetric Total Synthesis of (-)-Actinophyllic Acid [J].
Cai, Lingchao ;
Zhang, Kui ;
Kwon, Ohyun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (10) :3298-3301
[6]  
Carey R.J., 2007, Advanced Organic Chemistry Part A: Structure and Mechanisms
[7]   An Unexpected Phosphine-Catalyzed Regio- and Diastereoselective [4+1] Annulation Reaction of Modified Allylic Compounds with Activated Enones [J].
Chen, Zuliang ;
Zhang, Junliang .
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (07) :1542-1545
[8]   Phosphine-catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita-Baylis-Hillman acetates [J].
Cho, CW ;
Kong, JR ;
Krische, MJ .
ORGANIC LETTERS, 2004, 6 (08) :1337-1339
[9]   Enantioselective catalysis and complexity generation from allenoates [J].
Cowen, Bryan J. ;
Miller, Scott J. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3102-3116
[10]   Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4+2]-Annulation Reaction [J].
Danda, Adithi ;
Kesava-Reddy, Naredla ;
Golz, Christopher ;
Strohmann, Carsten ;
Kumar, Kamal .
ORGANIC LETTERS, 2016, 18 (11) :2632-2635