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

来源：

CHEMICAL REVIEWS | 2017年 / 117卷 / 05期

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

页码：4147 / 4181

页数：35

共 143 条

[1] Synthesis of original phosphine-sulfoxide ligands for asymmetric allylic alkylation [J].

Alvarado-Beltran, Isabel ;

Lozano Gonzalez, Mariana ;

Escudie, Yannick ;

Maerten, Eddy ;

Saffon-Merceron, Nathalie ;

Fabing, Isabelle ;

Alvarez Toledano, Cecilio ;

Baceiredo, Antoine .

TETRAHEDRON, 2016, 72 (13) :1662-1667

[2] N-tert-Butanesulfinyl imine and aromatic tertiary amide derived non-biaryl atropisomers as chiral ligands for silver-catalyzed endo-selective [3+2] cycloaddition of azomethine ylides with maleimides [J].

Bai, Xing-Feng ;

Zhang, Jin ;

Xia, Chun-Gu ;

Xu, Jian-Xing ;

Xu, Li-Wen .

TETRAHEDRON, 2016, 72 (21) :2690-2699

[3] Aromatic-Amide-Derived Nonbiaryl Atropisomer as Highly Efficient Ligand for Asymmetric Silver-Catalyzed [3+2] Cycloaddition [J].

Bai, Xing-Feng ;

Xu, Zheng ;

Xia, Chun-Gu ;

Zheng, Zhan-Jiang ;

Xu, Li-Wen .

ACS CATALYSIS, 2015, 5 (10) :6016-6020

[4] Aromatic Amide-Derived Non-Biaryl Atropisomers as Highly Efficient Ligands in Silver-Catalyzed Asymmetric Cycloaddition Reactions [J].

Bai, Xing-Feng ;

Song, Tao ;

Xu, Zheng ;

Xia, Chun-Gu ;

Huang, Wei-Sheng ;

Xu, Li-Wen .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (17) :5255-5259

[5] Chiral Sulfinamide/Achiral Sulfonic Acid Cocatalyzed Enantioselective Protonation of Enol Silanes [J].

Beck, Elizabeth M. ;

Hyde, Alan M. ;

Jacobsen, Eric N. .

ORGANIC LETTERS, 2011, 13 (16) :4260-4263

[6] Synthesis of phosphorylated sulfoximines and sulfinamides and their application as ligands in asymmetric metal catalysis [J].

Benetskiy, Eduard B. ;

Bolm, Carsten .

TETRAHEDRON-ASYMMETRY, 2011, 22 (03) :373-378

[7] Catalytic asymmetric carbon-carbon bond-forming reactions in aqueous media [J].

Bhowmick, Sudipto ;

Bhowmick, Kartick C. .

TETRAHEDRON-ASYMMETRY, 2011, 22 (23) :1945-1979

[8] C2-symmetric bissulfoximines as ligands in copper-catalyzed enantioselective Diels-Alder reactions [J].

Bolm, C ;

Martin, M ;

Simic, O ;

Verrucci, M .

ORGANIC LETTERS, 2003, 5 (04) :427-429

[9] A new class of C1-symmetric monosulfoximine ligands for enantioselective hetero Diels-Alder reactions [J].

Bolm, C ;

Verrucci, M ;

Simic, O ;

Cozzi, PG ;

Raabe, G ;

Okamura, H .

CHEMICAL COMMUNICATIONS, 2003, (22) :2826-2827

[10]

Bolm C, 2001, SYNLETT, P1878

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