Synthesis of Botryllamides and Lansiumamides via Ruthenium-Catalyzed Hydroamidation of Alkynes

被引:21
作者
Goossen, Lukas J. [1 ]
Blanchot, Mathieu [1 ]
Arndt, Matthias [1 ]
Salih, Kifah S. M. [1 ]
机构
[1] TU Kaiserslautern, Inst Organ Chem, D-67663 Kaiserslautern, Germany
关键词
alkyne; botryllamide; hydroamidation; lansamide; lansiumamide; ruthenium; ANTI-MARKOVNIKOV-ADDITION; STEREOSELECTIVE-SYNTHESIS; TYROSINE DERIVATIVES; SELECTIVE ADDITION; ENAMIDES; AMIDES; INHIBITORS; ALDEHYDES; ETHERS;
D O I
10.1055/s-0029-1219961
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ruthenium-catalyzed hydroamidations of alkynes allow a concise synthetic entry to both E-and Z-configured enamide natural products. This was demonstrated by the synthesis of botryllamides C and E, lansiumamides A and B, and lansamide I in 1-3 steps and 57-98% yield from simple, commercially available precursors.
引用
收藏
页码:1685 / 1687
页数:3
相关论文
共 49 条
[1]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[2]  
[Anonymous], 2006, ANGEW CHEM
[3]   Synthesis of enamides from aldehydes and amides [J].
Bayer, A ;
Maier, ME .
TETRAHEDRON, 2004, 60 (31) :6665-6677
[4]   Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].
Beller, M ;
Seayad, J ;
Tillack, A ;
Jiao, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398
[5]  
Beller M, 2004, ANGEW CHEM, V116, P3448
[6]   SYNTHETIC STUDIES OF THE CYCLOPROPYL IMINIUM ION REARRANGEMENT .3. APPLICATION OF THE CYCLOPROPYL ACYLIMINIUM ION REARRANGEMENT TO A CONCISE AND HIGHLY CONVERGENT SYNTHESIS OF (+/-)-LYCORINE [J].
BOECKMAN, RK ;
GOLDSTEIN, SW ;
WALTERS, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8250-8252
[7]   Formation of enamides via palladium(II)-catalyzed vinyl transfer from vinyl ethers to nitrogen nucleophiles [J].
Brice, JL ;
Meerdink, JE ;
Stahl, SS .
ORGANIC LETTERS, 2004, 6 (11) :1845-1848
[8]   Metal vinylidenes and allenylidenes in catalysis: Applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis [J].
Bruneau, C ;
Dixneuf, PH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (14) :2176-2203
[9]   Powerful control by organoruthenium catalysts of the regioselective addition to C(1) or C(2) of the prop-2-ynyl ethers CC triple bond [J].
Doucet, H ;
Derrien, N ;
Kabouche, Z ;
Bruneau, C ;
Dixneuf, PH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 551 (1-2) :151-157
[10]  
Dupau P, 1999, SYNLETT, P1832