Planar-Chiral Thioureas as Hydrogen-Bond Catalysts

被引：59

作者：

Schneider, Jakob F. ^{[1
]}

Falk, Florian C. ^{[1
]}

Froehlich, Roland ^{[2
]}

Paradies, Jan ^{[1
]}

机构：

[1] Karlsruhe Inst Technol, D-76131 Karlsruhe, Germany

[2] Univ Munster, D-48149 Munster, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 12期

关键词：

Thioureas; Hydrogen bonds; Cyclophanes; Organocatalysis; Chirality; ASYMMETRIC CATALYSIS; MACRO RINGS; LIGANDS; CARBENE; ORGANOCATALYSIS; DERIVATIVES; COMPLEXES; ACID;

D O I：

10.1002/ejoc.200901353

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the first enantiopure planar-chiral thiourea catalysts is herewith described. New catalysts 1-3 were applied in asymmetric transformations, such as the Friedel-Crafts alkylation of indole, as well as in the transfer hydrogenation of nitroolefins. Bifunctional catalysts 2 and 3 exhibit enhanced activity in the investigated reactions, demonstrating their potential for organic synthesis.

引用

页码：2265 / 2269

页数：5

共 50 条

[1] [2.2]Paracyclophane-Derived Planar-Chiral Hydrogen-Bond Receptors
Schneider, Jakob F.
Froehlich, Roland
Paradies, Jan
[J]. ISRAEL JOURNAL OF CHEMISTRY, 2012, 52 (1-2) : 76 - 91
[2] HYDROGEN-BOND BASICITY OF THIOAMIDES AND THIOUREAS
LAURENCE, C
BERTHELOT, M
LEQUESTEL, JY
ELGHOMARI, MJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (11): : 2075 - 2079
[3] Development of fluorinated chiral hydrogen-bond donor catalysts
Sprague, Daniel J.
Takenaka, Norito
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[4] Silanediols as Hydrogen-Bond Donor Catalysts
Izumiseki, Atsuto
[J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2015, 73 (04) : 386 - 387
[5] Enantioselective Synthesis of Planar-Chiral Compounds by Using Metal Catalysts
Ogawa, Narihito
[J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2014, 72 (07) : 832 - 833
[6] Asymmetric catalysis by chiral hydrogen-bond donors
Carreira, Erick M.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[7] Asymmetric catalysis by chiral hydrogen-bond donors
Taylor, MS
Jacobsen, EN
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (10) : 1520 - 1543
[8] Asymmetric catalysis by chiral hydrogen-bond donors
Jacobsen, Eric N.
Taylor, Mark S.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[9] REACTION OF DIIODOMETHANE WITH THIOUREAS WITHOUT AN INTRA-MOLECULAR HYDROGEN-BOND
RIED, W
MOSINGER, O
[J]. CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (01): : 155 - 167
[10] Planar-Chiral Cyclopentadienyl Rhodium Catalysts: Design Concept, Chiral Resolution Strategy, and Applications
Zhang, Chunhui
Jiang, Jijun
Huang, Xiaoyu
Wang, Jun
[J]. ACS CATALYSIS, 2023, 13 (15) : 10468 - 10473

← 1 2 3 4 5 →