Recent advances in cyclohydrocarbonylation reactions

被引:27
作者
Chiou, WH [1 ]
Lee, SY [1 ]
Ojima, I [1 ]
机构
[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA
关键词
catalysis; cyclohydrocarbonylation; hydroformylation; amidocarbonylation; cyclization; regioselectivity; aldehydes; regioselective; cascade; heterocycles; rhodium;
D O I
10.1139/v05-035
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This article describes recent advances in the cyclohydrocarbonylation reactions catalyzed by transition-metal complexes and their applications in organic synthesis as a review covering the relevant literature up to the middle of 2004. The reactions are categorized into four types, i.e., intramolecular amidocarbonylation reactions, intramolecular aminocarbonylation reactions, cyclohydrocarbonylation reactions involving carbon-nucleophiles, and other cyclohydrocarbonylation reactions. Cyclohydrocarbonylation reactions provide efficient routes to various monocyclic, bicyclic, and polycyclic compounds as a one-step cascade process or a one-pot process. Reaction mechanisms for these cascade processes are discussed as needed for clarification. The heterocyclic and carbocyclic compounds, thus obtained, can be further transformed to specific targets. Examples of such applications are also discussed.
引用
收藏
页码:681 / 692
页数:12
相关论文
共 47 条
[1]   SYNTHESIS OF PROLINE AND 2-PIPERIDINECARBOXYLIC ACID VIA COBALT-CATALYZED ISOMERIZATION-CARBONYLATION OF N-ACYL UNSATURATED CYCLIC AMINES [J].
AMINO, Y ;
NISHI, S ;
IZAWA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (02) :620-623
[2]   SYNTHESIS OF ALPHA,OMEGA-DIAMINO ACIDS VIA AMIDOCARBONYLATION REACTION - NOVEL SYNTHESIS OF LYSINE, ORNITHINE, AND THEIR ANALOGS [J].
AMINO, Y ;
IZAWA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (02) :613-619
[3]  
[Anonymous], 2000, ORGANIC REACTIONS
[4]  
BAFFACKER L, 1998, TETRAHEDRON, V54, P4493
[5]   ASYMMETRIC HYDROFORMYLATION AND HYDROCARBOXYLATION OF ENAMIDES - SYNTHESIS OF ALANINE AND PROLINE [J].
BECKER, Y ;
EISENSTADT, A ;
STILLE, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (11) :2145-2151
[6]   Rhodium-catalysed hydroformylation and carbonylation of N-alkenyl-1,3-diaminopropanes [J].
Bergmann, DJ ;
Campi, EM ;
Jackson, WR ;
McCubbin, QJ ;
Patti, AF .
TETRAHEDRON, 1997, 53 (51) :17449-17460
[7]   High yields of diazabicycloalkanes and oxazabicycloalkanes containing medium and large rings from rhodium-catalysed hydroformylation reactions without the need for high dilution conditions [J].
Bergmann, DJ ;
Campi, EM ;
Jackson, WR ;
Patti, AF .
CHEMICAL COMMUNICATIONS, 1999, (14) :1279-1280
[8]  
Billig E., 1988, U.S. Patent, Patent No. [4,769,498, 4769498]
[9]  
Breit B., 2001, SYNTHESIS-STUTTGART, V1, P1
[10]   THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .61. THE PREPARATION OF QUINAZOLINES AND QUINAZOLINONES INVOLVING RHODIUM-CATALYZED HYDROFORMYLATION OF ALKENYL ANILINES [J].
CAMPI, EM ;
JACKSON, WR ;
MCCUBBIN, QJ ;
TRNACEK, AE .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (06) :1061-1070