Rhodium-catalyzed addition of alkynes to activated ketones and aldehydes

被引:42
作者
Dhondi, PK [1 ]
Chisholm, JD [1 ]
机构
[1] Syracuse Univ, Dept Chem, Ctr Sci & Technol 1 014, Syracuse, NY 13244 USA
关键词
D O I
10.1021/ol0525260
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The rhodium-catalyzed addition of alkynes to 1,2-diketones, 1,2-ketoesters, and aldehydes provides a method for the synthesis of tertiary alkynyl alcohols under mild conditions. The reaction tolerates many functional groups (such as carboxylic acids) that are incompatible with other methods. The alkyne addition reaction proceeds best using bulky phosphine ligands such as 2-(di-tert-butylphosphino)biphenyl. This method fills a void in the more common zinc-catalyzed processes, which give poor yields with enolizable 1,2-dicarbonyl substrates.
引用
收藏
页码:67 / 69
页数:3
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共 34 条
[1]   SYNTHESIS AND STRUCTURE OF TRANS-[MCL(=C=CHR)(PIPR3)2] (M=RH,IR) - THE 1ST SQUARE-PLANAR VINYLIDENEMETAL COMPLEXES [J].
ALONSO, FJG ;
HOHN, A ;
WOLF, J ;
OTTO, H ;
WERNER, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (05) :406-408
[2]   A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].
Anand, NK ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688
[3]   BINOL catalyzed enantioselective addition of titanium phenylacetylide to aromatic ketones [J].
Cozzi, PG ;
Alesi, S .
CHEMICAL COMMUNICATIONS, 2004, (21) :2448-2449
[4]   Acetylenes in catalysis: Enantioselective additions to carbonyl groups and imines and applications beyond [J].
Cozzi, PG ;
Hilgraf, R ;
Zimmermann, N .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (20) :4095-4105
[5]   Enantioselective total synthesis of (+)-gigantecin: Exploiting the asymmetric glycolate aldol reaction [J].
Crimmins, MT ;
She, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (40) :12790-12791
[6]   Substitution and oxidative addition reactions of the monoolefin complex Rh(acac)(cyclooctene)(PCy(3)) including the x-ray structure analyses of Rh(acac)(PCy(3))(2) and [Rh(acac){(E)-CH=CHCy}(PCy(3))(2)]BF4 [J].
Esteruelas, MA ;
Lahoz, FJ ;
Onate, E ;
Oro, LA ;
Rodriguez, L ;
Steinert, P ;
Werner, H .
ORGANOMETALLICS, 1996, 15 (15) :3436-3444
[7]   Infrared spectroscopic investigations on the metallation of terminal alkynes by Zn(OTf)2 [J].
Fässler, R ;
Tomooka, CS ;
Frantz, DE ;
Carreira, EM .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) :5843-5845
[8]   Leucascandrolide A: Synthesis and related studies [J].
Fettes, A ;
Carreira, EM .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9274-9283
[9]   Highly active and selective catalysts for the formation of α-aryl ketones [J].
Fox, JM ;
Huang, XH ;
Chieffi, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1360-1370
[10]   Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes [J].
Frantz, DE ;
Fässler, R ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1806-1807