Chiral Organosulfur Ligands/Catalysts with a Stereogenic Sulfur Atom: Applications in Asymmetric Synthesis

被引:346
作者
Otocka, Sylwia [1 ,2 ]
Kwiatkowska, Malgorzata [1 ]
Madalinska, Lidia [1 ]
Kielbasinski, Piotr [1 ]
机构
[1] Polish Acad Sci, Dept Heteroorgan Chem, Ctr Mol & Macromol Studies, Sienkiewicza 112, PL-90363 Lodz, Poland
[2] Med Univ Lodz, Dept Biol Struct, Zeligowskiego 7-9, PL-90752 Lodz, Poland
关键词
N-SULFINYL UREA; DIELS-ALDER REACTIONS; CATALYZED ENANTIOSELECTIVE ADDITION; NON-BIARYL ATROPISOMERS; BIS-SULFOXIDE LIGAND; AZA-HENRY REACTION; ARYLBORONIC ACIDS; OLEFIN LIGANDS; ALLYL TRICHLOROSILANE; EFFICIENT LIGANDS;
D O I
10.1021/acs.chemrev.6b00517
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric synthesis, in which chiral organocatalysts or metal complexes with chiral ligands are used, has become the most valuable methodology for the preparation of enantiomerically pure organic compounds. Among such catalysts/ligands, a growing number constitute various organosulfur compounds. This Review provides comprehensive and critical information on the plethora of sulfur-based chiral ligands and organocatalysts used in asymmetric synthesis, which have been published within the last 15 years. However, it is confined to the presentation of only those chiral catalysts/ligands that possess a stereogenic sulfur atom and includes sulfoxides, sulfinamides, N-sulfinyl ureas, sulfoximines, and some related S-chiral derivatives.
引用
收藏
页码:4147 / 4181
页数:35
相关论文
共 143 条
[11]   Highly enantioselective hetero-Diels-Alder reactions catalyzed by a C2-symmetric bis(sulfoximine) Copper(II) complex [J].
Bolm, C ;
Simic, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (16) :3830-3831
[12]   Optically active sulfoximines in enantioselective palladium catalysis [J].
Bolm, C ;
Kaufmann, D ;
Zehnder, M ;
Neuburger, M .
TETRAHEDRON LETTERS, 1996, 37 (23) :3985-3988
[13]  
Bolm C., 2007, ASYMMETRIC SYNTHESIS, P149, DOI DOI 10.1002/9783527610648.CH2A
[14]   Chiral N-phosphino sulfinamide ligands in rhodium(I)-catalyzed [2+2+2] cycloaddition reactions [J].
Brun, Sandra ;
Parera, Magda ;
Pla-Quintana, Anna ;
Roglans, Anna ;
Leon, Thierry ;
Achard, Thierry ;
Sola, Jordi ;
Verdaguer, Xavier ;
Riera, Antoni .
TETRAHEDRON, 2010, 66 (46) :9032-9040
[15]   Unprecedented Selectivity via Electronic Substrate Recognition in the 1,4-Addition to Cyclic Olefins Using a Chiral Disulfoxide Rhodium Catalyst [J].
Buergi, Justus J. ;
Mariz, Ronaldo ;
Gatti, Michele ;
Drinkel, Emma ;
Luan, Xinjun ;
Blumentritt, Sascha ;
Linden, Anthony ;
Dorta, Reto .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (15) :2768-2771
[16]   Enantiopure sulfoxides: recent applications in asymmetric synthesis [J].
Carmen Carreno, M. ;
Hernandez-Torres, Gloria ;
Ribagorda, Maria ;
Urbano, Antonio .
CHEMICAL COMMUNICATIONS, 2009, (41) :6129-6144
[17]   CATALYTIC ACTIVITY OF CHIRAL BETA-HYDROXYSULFOXIDES IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE [J].
CARRENO, MC ;
RUANO, JLG ;
MAESTRO, MC ;
CABREJAS, LMM .
TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :727-734
[18]   Sulfinamide Phosphinates as Chiral Catalysts for the Enantioselective Organocatalytic Reduction of Imines [J].
Chelouan, Ahmed ;
Recio, Rocio ;
Borrego, Lorenzo G. ;
Alvarez, Eleuterio ;
Khiar, Noureddine ;
Fernandez, Inmaculada .
ORGANIC LETTERS, 2016, 18 (13) :3258-3261
[19]   Chiral sulfoxide-olefin ligands: tunable stereoselectivity in Rh-catalyzed asymmetric 1,4-additions [J].
Chen, Guihua ;
Gui, Jiangyang ;
Cao, Peng ;
Liao, Jian .
TETRAHEDRON, 2012, 68 (15) :3220-3224
[20]   Chiral Sulfoxide-Olefin Ligands: Completely Switchable Stereoselectivity in Rhodium-Catalyzed Asymmetric Conjugate Additions [J].
Chen, Guihua ;
Gui, Jiangyang ;
Li, Liangchun ;
Liao, Jian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7681-7685