Steric tuning of C2-symmetric chiral N-heterocyclic carbene in gold-catalyzed asymmetric cyclization of 1,6-enynes

被引：27

作者：

Yamada, Ken-ichi ^{[1
]}

Matsumoto, Yasumasa ^{[1
]}

Selim, Khalid B. ^{[2
]}

Yamamoto, Yasutomo ^{[3
]}

Tomioka, Kiyoshi ^{[3
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Mansoura Univ, Fac Pharm, Dept Organ Pharmaceut Chem, Mansoura 35516, Egypt

[3] Doshisha Womens Coll Liberal Arts, Fac Pharmaceut Sci, Kodo, Kyotanabe 6100395, Japan

来源：

TETRAHEDRON | 2012年 / 68卷 / 22期

关键词：

ENANTIOSELECTIVE INTRAMOLECULAR HYDROAMINATION; TRANSITION METAL-COMPLEXES; ALDOL REACTION; C-C; ENYNES; LIGAND; CYCLOISOMERIZATION; ALKOXYCYCLIZATION; PLATINUM; HYDROALKOXYLATION;

D O I：

10.1016/j.tet.2012.03.107

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Steric tuning of C-2-symmetric chiral N-heterocyclic carbene (NHC) was performed in Au(I)-catalyzed asymmetric cyclization of 1,6-enyne. Higher enantioselectivity was realized when chiral NHC AuCl/AgSbF6 catalysts whose N-substituent on the NHC overlays the Au-Cl bond was utilized. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：4159 / 4165

页数：7

共 77 条

[1] Gold-Catalyzed [4C+2C] Cycloadditions of Allenedienes, including an Enantioselective Version with New Phosphoramidite-Based Catalysts: Mechanistic Aspects of the Divergence between [4C+3C] and [4C+2C] Pathways [J].

Alonso, Isaac ;

Trillo, Beatriz ;

Lopez, Fernando ;

Montserrat, Sergi ;

Ujaque, Gregori ;

Castedo, Luis ;

Lledos, Agusti ;

Mascarenas, Jose L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) :13020-13030

[2] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[3] Synthesis and Catalytic Activity of Gold Chiral Nitrogen Acyclic Carbenes and Gold Hydrogen Bonded Heterocyclic Carbenes in Cyclopropanation of Vinyl Arenes and in Intramolecular Hydroalkoxylation of Allenes [J].

Bartolome, Camino ;

Garcia-Cuadrado, Domingo ;

Ramiro, Zoraida ;

Espinet, Pablo .

INORGANIC CHEMISTRY, 2010, 49 (21) :9758-9764

[4] Golden opportunities in stereoselective catalysis [J].

Bongers, Nadine ;

Krause, Norbert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2178-2181

[5] Stable carbenes [J].

Bourissou, D ;

Guerret, O ;

Gabbaï, FP ;

Bertrand, G .

CHEMICAL REVIEWS, 2000, 100 (01) :39-91

[6] Enantioselective synthesis of diversely substituted quaternary 1,4-benzodiazepin-2-ones and 1,4-benzodiazepine-2,5-diones [J].

Carlier, Paul R. ;

Zhao, Hongwu ;

MacQuarrie-Hunter, Stephanie L. ;

DeGuzman, Joseph C. ;

Hsu, Danny C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (47) :15215-15220

[7] Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis [J].

César, V ;

Bellemin-Laponnaz, S ;

Gade, LH .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :619-636

[8] Asymmetric Au(I)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes [J].

Chao, Chung-Meng ;

Beltrami, Denis ;

Toullec, Patrick Y. ;

Michelet, Veronique .

CHEMICAL COMMUNICATIONS, 2009, (45) :6988-6990

[9] Towards asymmetric Au-catalyzed hydroxy- and alkoxycyclization of 1,6-enynes [J].

Chao, Chung-Meng ;

Genin, Emilie ;

Toullec, Patrick Y. ;

Genet, Jean-Pierre ;

Michelet, Veronique .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (04) :538-545

[10] Asymmetric Gold-Catalyzed Hydroarylation/Cyclization Reactions [J].

Chao, Chung-Meng ;

Vitale, Maxime R. ;

Toullec, Patrick Y. ;

Genet, Jean-Pierre ;

Michelet, Veronique .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (06) :1319-1323

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