Asymmetric Synthesis of (Triaryl)methylamines by Rhodium-Catalyzed Addition of Arylboroxines to Cyclic N-Sulfonyl Ketimines

被引：194

作者：

Nishimura, Takahiro ^{[1
]}

Noishiki, Akira ^{[1
]}

Tsui, Gavin Chit ^{[1
]}

Hayashi, Tamio ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 11期

关键词：

CHIRAL DIENE LIGANDS; QUATERNARY CARBON CENTERS; ENANTIOSELECTIVE SYNTHESIS; TOLUENE-2; ALPHA-SULTAM AUXILIARIES; NUCLEOPHILIC-ADDITION; EFFICIENT SYNTHESIS; ARYLATION; IMINES; ACIDS; REAGENTS;

D O I：

10.1021/ja300697c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Asymmetric addition of arylboroxines to cyclic N-sulfonyl ketimines proceeded in the presence of a rhodium catalyst coordinated with a chiral diene ligand to give high yields of benzosultams, where a triaryl-substituted stereogenic carbon center was created with high enantioselectivity (93-99% ee). The chiral benzosultams were transformed into the chiral (triaryl)methylamines by breaking the cyclic structure.

引用

页码：5056 / 5059

页数：4

共 78 条

[1] Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines [J].

Akullian, LC ;

Snapper, ML ;

Hoveyda, AH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4244-4247

[2]

Baker D. C., 2002, U.S. Patent, Patent No. [6,353,112 Bl, 6353112]

[3] Stereoselective synthesis of N-heterocycles: application of the asymmetric Cu-catalyzed addition of Et2Zn to functionalized alkyl and aryl imines [J].

Bonnaventure, Isabelle ;

Charette, Andre B. .

TETRAHEDRON, 2009, 65 (26) :4968-4976

[4] Development of Binaphthyl-Based Chiral Dienes for Rhodium(I)-Catalyzed Asymmetric Arylation of N,N-Dimethylsulfamoyl-Protected Aldimines [J].

Cao, Ziping ;

Du, Haifeng .

ORGANIC LETTERS, 2010, 12 (11) :2602-2605

[5] Asymmetric Hydrogenation of Cyclic N-Sulfonylimines with Phosphine-Free Chiral Cationic Ru-MsDPEN Catalysts [J].

Chen Fei ;

Li Zhiwei ;

He Yanmei ;

Fan Qinghua .

CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (09) :1529-1532

[6] NOVEL ELECTRONIC EFFECTS OF REMOTE SUBSTITUENTS ON THE OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES [J].

COREY, EJ ;

HELAL, CJ .

TETRAHEDRON LETTERS, 1995, 36 (50) :9153-9156

[7] Bis-Sulfamyl Imines: Potent Substrates for Asymmetric Additions of Arylboroxines under Rhodium Catalysis [J].

Crampton, Rosemary ;

Woodward, Simon ;

Fox, Martin .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (06) :903-906

[8] Highly Enantioselective Arylation of N-Tosylalkylaldimines Catalyzed by Rhodium-Diene Complexes [J].

Cui, Zhe ;

Yu, Hong-Jie ;

Yang, Rui-Feng ;

Gao, Wen-Yun ;

Feng, Chen-Guo ;

Lin, Guo-Qiang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (32) :12394-12397

[9] CHEMISTRY OF OXAZIRIDINES .13. SYNTHESIS, REACTIONS, AND PROPERTIES OF 3-SUBSTITUTED 1,2-BENZISOTHIAZOLE 1,1-DIOXIDE OXIDES [J].

DAVIS, FA ;

TOWSON, JC ;

VASHI, DB ;

THIMMAREDDY, R ;

MCCAULEY, JP ;

HARAKAL, ME ;

GOSCINIAK, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1254-1261

[10] Chiral olefins as steering ligands in asymmetric catalysis [J].

Defieber, Christian ;

Gruetzmacher, Hansjoerg ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (24) :4482-4502

← 1 2 3 4 5 6 7 8 →