Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles

被引：210

作者：

Miura, Tomoya ^{[1
]}

Biyajima, Tsuneaki ^{[1
]}

Fujii, Tetsuji ^{[1
]}

Murakami, Masahiro ^{[1
]}

机构：

[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Katsura, Kyoto 6158510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 01期

关键词：

ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC HYDROGENATION; ANNULATION REACTIONS; PRACTICAL SYNTHESIS; EFFICIENT SYNTHESIS; FUSED HETEROCYCLES; CARBONYL-COMPOUNDS; AZAVINYL CARBENES; PEPTIDYL KETONES; 1,2,3-BENZOTRIAZIN-4(3H)-ONES;

D O I：

10.1021/ja2104203

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce alpha-amino ketones in high yield. An intermediary alpha-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.

引用

收藏

页码：194 / 196

页数：3

相关论文

共 56 条

[1] Concise synthesis of 1H-pyrazin-2-ones and 2-aminopyrazines [J].

Adam, I ;

Orain, D ;

Meier, P .

SYNLETT, 2004, (11) :2031-2033

[2] Catalytic enantioselective Amination of silyl enol ethers using chiral Dirhodium(II) carboxylates: Asymmetric formal synthesis of (-)-metazocine [J].

Anada, Masahiro ;

Tanaka, Masahiko ;

Washio, Takuya ;

Yamawaki, Minoru ;

Abe, Takumi ;

Hashimoto, Shunichi .

ORGANIC LETTERS, 2007, 9 (22) :4559-4562

[3] A stereospecific access to allylic systems using rhodium(II)-vinyl carbenoid insertion into Si-H, O-H, and N-H bonds [J].

Bulugahapitiya, P ;

Landais, Y ;

ParraRapado, L ;

Planchenault, D ;

Weber, V .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1630-1641

[4] Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides [J].

Cassidy, Michael P. ;

Raushel, Jessica ;

Fokin, Valery V. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3154-3157

[5] Rh-Catalyzed Transannulation of N-Tosyl-1,2,3-Triazoles with Terminal Alkynes [J].

Chattopadhyay, Buddhadeb ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2011, 13 (14) :3746-3749

[6] ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE BETA-AMINOALCOHOLS VIA ASYMMETRIC REDUCTION [J].

CHO, BT ;

CHUN, YS .

TETRAHEDRON-ASYMMETRY, 1992, 3 (03) :341-342

[7] Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water [J].

Cho, SH ;

Yoo, EJ ;

Bae, L ;

Chang, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :16046-16047

[8] Regiodivergent metal-catalyzed rearrangement of 3-iminocyclopropenes into N-fused heterocycles [J].

Chuprakov, Stepan ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2007, 9 (22) :4463-4466

[9] Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles [J].

Chuprakov, Stepan ;

Hwang, Frank W. ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) :4757-4759

[10] Catalytic Asymmetric C-H Insertions of Rhodium(II) Azavinyl Carbenes [J].

Chuprakov, Stepan ;

Malik, Jamal A. ;

Zibinsky, Mikhail ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (27) :10352-10355

← 1 2 3 4 5 6 →