Catalytic Enantioselective Desymmetrization Reactions to All-Carbon Quaternary Stereocenters

被引:646
作者
Zeng, Xing-Ping [1 ]
Cao, Zhong-Yan [1 ]
Wang, Yu-Hui [1 ]
Zhou, Feng [1 ]
Zhou, Jian [1 ,2 ,3 ]
机构
[1] E China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
[2] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[3] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
关键词
C-C BOND; ASYMMETRIC TOTAL-SYNTHESIS; TRICYCLIC BETA-LACTONES; STEREOGENIC CENTER; WIELAND-MIESCHER; H ARYLATION; AMINO-ACID; INTERMOLECULAR DESYMMETRIZATION; POLYCYCLIC DERIVATIVES; EFFICIENT CONSTRUCTION;
D O I
10.1021/acs.chemrev.6b00094
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This Review summarizes the advances in the construction of all-carbon quaternary stereocenters via catalytic enantioselective desymmetrization of prochiral and mesa-compounds, highlights the power and potential of this strategy in the total synthesis of natural products and biologically active compounds, and outlines the synthetic opportunities still available.
引用
收藏
页码:7330 / 7396
页数:67
相关论文
共 242 条
[21]   Enantioselective Copper(I)-Catalyzed Borylative Aldol Cyclizations of Enone Diones [J].
Burns, Alan R. ;
Gonzalez, Jorge Solana ;
Lam, Hon Wai .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (43) :10827-10831
[22]   I-AMINOCYCLOPROPANE-I-CARBOXYLIC ACID - NEW AMINO-ACID IN PERRY PEARS AND CIDER APPLES [J].
BURROUGHS, LF .
NATURE, 1957, 179 (4555) :360-361
[23]   Enantioselective desymmetrizing palladium catalyzed carbonylation reactions: the catalytic asymmetric synthesis of quaternary carbon center containing 1,3-dienes [J].
Byrne, Simon J. ;
Fletcher, Anthony J. ;
Hebeisen, Paul ;
Willis, Michael C. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (04) :758-760
[24]   Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds [J].
Cativiela, C ;
Diaz-de-Villegas, MD .
TETRAHEDRON-ASYMMETRY, 1998, 9 (20) :3517-3599
[25]   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
[26]   Recent advances in the total synthesis of cyclopropane-containing natural products [J].
Chen, David Y. -K. ;
Pouwer, Rebecca H. ;
Richard, Jean-Alexandre .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (13) :4631-4642
[27]   Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds [J].
Chen, Feng ;
Wang, Teng ;
Jiao, Ning .
CHEMICAL REVIEWS, 2014, 114 (17) :8613-8661
[28]   Asymmetric alcoholysis of cyclic anhydrides [J].
Chen, YG ;
McDaid, P ;
Deng, L .
CHEMICAL REVIEWS, 2003, 103 (08) :2965-2983
[29]   Enantio- and Diastereoselective Assembly of Tetrahydrofuran and Tetrahydropyran Skeletons with All-Carbon-Substituted Quaternary Stereocenters [J].
Chen, Zhilong ;
Sun, Jianwei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (51) :13593-13596
[30]   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