Catalytic synthesis of chiral organoheteroatom compounds of silicon, phosphorus, and sulfur via asymmetric transition metal-catalyzed C-H functionalization

被引:149
作者
Cui, Yu-Ming [1 ]
Lin, Yan [1 ]
Xu, Li-Wen [1 ,2 ]
机构
[1] Hangzhou Normal Univ, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou 311121, Zhejiang, Peoples R China
[2] Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat, Lanzhou Inst Chem Phys, Lanzhou 730000, Peoples R China
关键词
C-H activation; Asymmetric catalysis; Homogeneous catalysis; Transition metal catalysis; Organoheteroatom compounds; PROTON-ABSTRACTION MECHANISM; CROSS-COUPLING REACTIONS; ENANTIOSELECTIVE SYNTHESIS; DEHYDROGENATIVE SILYLATION; BOND FORMATION; STEREOGENIC DIBENZOSILOLES; REGIOSELECTIVE SILYLATION; LIGANDS; ACTIVATION; ARYLATION;
D O I
10.1016/j.ccr.2016.09.011
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral Si-, P-, and S-containing organic compounds with central, planar, and axial chiralities have found a plethora of applications in various fields of chemistry. Despite significant efforts to explore new catalytic methodologies and synthetic applications to access such compounds, there are still only a few examples which are low in number and limited in diversity. The catalytic construction of Si-, P-, and S-stereogenic organoheteroatom compounds is undoubtedly one of the most exciting and challenging aspects in asymmetric catalysis and the application of catalytic asymmetric C-H activation reaction for the construction of chiral organoheteroatom compounds is still in its infancy. In this Review, we highlighted the main progress on the corresponding catalytic asymmetric reactions that apply to the construction of Si-, P-, and S-stereogenic centers and related chiral organoheteroatom compounds in a catalytic C-H activation fashion. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:37 / 52
页数:16
相关论文
共 123 条
[2]   Synthetic Routes to Chiral Nonracemic and Racemic Dihydro- And Tetrahydrothiophenes [J].
Benetti, Simonetta ;
De Risi, Carmela ;
Pollini, Gian P. ;
Zanirato, Vinicio .
CHEMICAL REVIEWS, 2012, 112 (04) :2129-2163
[3]   Palladium-catalyzed asymmetric phosphination. Scope, mechanism, and origin of enantioselectivity [J].
Blank, Natalia F. ;
Moncarz, Jillian R. ;
Brunker, Tim J. ;
Scriban, Corina ;
Anderson, Brian J. ;
Amir, Omar ;
Glueck, David S. ;
Zakharov, Lev N. ;
Golen, James A. ;
Incarvito, Christopher D. ;
Rheingold, Arnold L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) :6847-6858
[4]  
Borner A., 2008, PHOSPHORUS LIGANDS A, V1-3
[5]   Cyclocarbopalladation:: Sequential cyclization and C-H activation/Stille cross-coupling in the Pd-5-exo-dig reaction [J].
Bour, C ;
Suffert, J .
ORGANIC LETTERS, 2005, 7 (04) :653-656
[6]   Palladium(II)-Catalyzed Highly Enantioselective C-H Arylation of Cyclopropylmethylamines [J].
Chan, Kelvin S. L. ;
Fu, Hai-Yan ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (05) :2042-2046
[7]   Dehydrogenative coupling involving P(O)-H bonds: a powerful way for the preparation of phosphoryl compounds [J].
Chen, Tieqiao ;
Zhang, Ji-Shu ;
Han, Li-Biao .
DALTON TRANSACTIONS, 2016, 45 (05) :1843-1849
[8]   Catalytic Silylation of Unactivated C-H Bonds [J].
Cheng, Chen ;
Hartwig, John F. .
CHEMICAL REVIEWS, 2015, 115 (17) :8946-8975
[9]   Pd(II)-Catalyzed Enantioselective C-H Activation/C-O Bond Formation: Synthesis of Chiral Benzofuranones [J].
Cheng, Xiu-Fen ;
Li, Yan ;
Su, Yi-Ming ;
Yin, Feng ;
Wang, Jian-Yong ;
Sheng, Jie ;
Vora, Harit U. ;
Wang, Xi-Sheng ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) :1236-1239
[10]   Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds [J].
Cherney, Alan H. ;
Kadunce, Nathaniel T. ;
Reisman, Sarah E. .
CHEMICAL REVIEWS, 2015, 115 (17) :9587-9652