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
[71]   Core-Structure-Motivated Design of a Phosphine-Catalyzed [3+2] Cycloaddition Reaction: Enantioselective Syntheses of Spirocyclopenteneoxindoles [J].
Tan, Bin ;
Candeias, Nuno R. ;
Barbas, Carlos F., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (13) :4672-4675
[72]   Phosphine-Catalyzed [4+1] Annuiation between α,β-Unsaturated Imines and Allylic Carbonates: Synthesis of 2-Pyrroilines [J].
Tian, Junjun ;
Zhou, Rong ;
Sun, Haiyun ;
Song, Haibin ;
He, Zhengjie .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07) :2374-2378
[73]   Phosphine-catalyzed [4+2] annulation: Synthesis of cyclohexenes [J].
Tran, Yang S. ;
Kwon, Ohyun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) :12632-+
[74]   INTERNAL REDOX CATALYZED BY TRIPHENYLPHOSPHINE [J].
TROST, BM ;
KAZMAIER, U .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) :7933-7935
[75]   Enantioselective acylations catalyzed by chiral phosphines [J].
Vedejs, E ;
Daugulis, O ;
Diver, ST .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :430-431
[76]   2-Phospha[3]ferrocenophanes with Planar Chirality: Synthesis and Use in Enantioselective Organocatalytic [3+2] Cyclizations [J].
Voituriez, Arnaud ;
Panossian, Armen ;
Fleury-Bregeot, Nicolas ;
Retailleau, Pascal ;
Marinetti, Angela .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (43) :14030-+
[77]   Phosphine Organocatalysis for the Synthesis of Spirocyclic Compounds [J].
Voituriez, Arnaud ;
Marinetti, Angela ;
Gicquel, Maxime .
SYNLETT, 2015, 26 (02) :142-166
[78]   An Organocatalytic [3+2] Cyclisation Strategy for the Highly Enantioselective Synthesis of Spirooxindoles [J].
Voituriez, Arnaud ;
Pinto, Nathalie ;
Neel, Mathilde ;
Retailleau, Pascal ;
Marinetti, Angela .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (42) :12541-12544
[79]   Phosphine-Catalyzed [2+4] Annulation of Allenoates with Thiazolone-Derived Alkenes: Synthesis of Functionalized 6,7-Dihydro-5H-pyrano[2,3-d]thiazoles [J].
Wang, Chang ;
Gao, Zhenzhen ;
Zhou, Leijie ;
Yuan, Chunhao ;
Sun, Zhanhu ;
Xiao, Yumei ;
Guo, Hongchao .
ORGANIC LETTERS, 2016, 18 (14) :3418-3421
[80]   Construction of adjacent spiro-quaternary and tertiary stereocenters through phosphine-catalyzed asymmetric [3+2] annulation of allenoates with alkylidene azlactones [J].
Wang, De ;
Wei, Yin ;
Shi, Min .
CHEMICAL COMMUNICATIONS, 2012, 48 (22) :2764-2766