Ruthenium-Catalyzed Addition of Primary Amides to Alkynes: A Stereoselective Synthesis of Secondary Enamides

被引：23

作者：

Goossen, Lukas J. ^{[1
]}

Blanchot, Mathieu ^{[1
]}

Salih, Kifah S. M. ^{[1
]}

Goosen, Kaethe ^{[1
]}

机构：

[1] Tech Univ Kaiserslautern, Fachbereich Chem, D-67663 Kaiserslautern, Germany

来源：

SYNTHESIS-STUTTGART | 2009年 / 13期

关键词：

alkynes; amides; enamides; hydroamidation; ruthenium; CARBOXYLIC-ACIDS; HYDROAMINATION; DERIVATIVES; ALDEHYDES; HYDRATION;

D O I：

10.1055/s-0029-1216847

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The anti-Markovnikov addition of primary amides to terminal alkynes under the formation of 7 configured secondary enamides is efficiently promoted by a catalyst system generated in situ from bis(2-methallyl)(cycloocta-1,5-diene)ruthenium(II), 1,4-bis(dicyclohexylphosphino)butane, and ytterbium triflate. The thermodynamically more stable E-isomers are accessible by combining the above hydroamidation with an in situ double-bond isomerization reaction, using triethylamine and molecular sieves.

引用

页码：2283 / 2288

页数：6

共 28 条

[11] Regiocontrolled Ru-catalyzed addition of carboxylic acids to alkynes: practical protocols for the synthesis of vinyl esters [J].

Goossen, LJ ;

Paetzold, J ;

Koley, D .

CHEMICAL COMMUNICATIONS, 2003, (06) :706-707

[12] Synthesis of Secondary Enamides by Ruthenium-Catalyzed Selective Addition of Amides to Terminal Alkynes [J].

Goossen, Lukas J. ;

Salih, Kifah S. M. ;

Blanchot, Mathieu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) :8492-8495

[13] Ruthenium-Catalyzed Stereoselective anti-Markovnikov-Addition of Thioamides to Alkynes [J].

Goossen, Lukas J. ;

Blanchot, Mathieu ;

Salih, Kifah S. M. ;

Karch, Ralf ;

Rivas-Nass, Andreas .

ORGANIC LETTERS, 2008, 10 (20) :4497-4499

[14] Ru-catalyzed stereoselective addition of imides to alkynes [J].

Goossen, Lukas J. ;

Blanchot, Mathieu ;

Brinkmann, Claus ;

Goossen, Kathe ;

Karch, Ralph ;

Rivas-Nass, Andreas .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9506-9509

[15] A Practical and Effective Ruthenium Trichloride-Based Protocol for the Regio- and Stereoselective Catalytic Hydroamidation of Terminal Alkynes [J].

Goossen, Lukas J. ;

Arndt, Matthias ;

Blanchot, Mathieu ;

Rudolphi, Felix ;

Menges, Fabian ;

Niedner-Schatteburg, Gereon .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (17) :2701-2707

[16] Enamide-olefin ring-closing metathesis [J].

Kinderman, SS ;

van Maarseveen, JH ;

Schoemaker, HE ;

Hiemstra, H ;

Rutjes, FPJT .

ORGANIC LETTERS, 2001, 3 (13) :2045-2048

[17]

KONDO T, 1995, CHEM COMMUN, P413

[18] CINNAMAMIDE DERIVATIVES FROM CLAUSENA-LANSIUM [J].

LIN, JH .

PHYTOCHEMISTRY, 1989, 28 (02) :621-622

[19] BETA-PHENYLETHYLAMINE-DERIVED AMIDES FROM PIPER-GUAYRANUM [J].

MAXWELL, A ;

RAMPERSAD, D .

JOURNAL OF NATURAL PRODUCTS, 1989, 52 (02) :411-414

[20] SELECTIVE ADDITION OF UNSATURATED CARBOXYLIC-ACIDS TO TERMINAL ACETYLENES CATALYZED BY BIS(ETA-5-CYCLOOCTADIENYL)RUTHENIUM(II)-TRI-NORMAL-BUTYL-PHOSPHINE - A NOVEL SYNTHESIS OF ENOL ESTERS [J].

MITSUDO, T ;

HORI, Y ;

WATANABE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1566-1568

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