Synthesis of hydronaphthalenes through coupling of enyne-carbonyl compounds that contain pendant alkane groups with Fischer carbene complexes

被引:4
作者
Patti, Rajesh Kumar [1 ]
Duan, Shaofeng [1 ]
Camacho-Davila, Alejandro [1 ]
Waynant, Kris [1 ]
Dunn, Kenneth A. [1 ]
Herndon, James W. [1 ]
机构
[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA
关键词
DIELS-ALDER REACTION; FURAN-DIENE; CYCLOADDITION CHEMISTRY; DERIVATIVES; ALDEHYDES; SYSTEMS; KETONES;
D O I
10.1016/j.tetlet.2010.05.049
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The coupling of enyne-carbonyl compounds that contain pendant alkene groups with Fischer carbene complexes to afford furans that contain pendant alkene groups is described. Subsequent intramolecular Diels-Alder reactions are effective in selected cases, resulting in hydronaphthalene systems after dehydration. Although the Diels-Alder event is thermodynamically unfavorable, the overall transformation of alkene-furans to dihydronaphthalenes is a favorable process. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3682 / 3684
页数:3
相关论文
共 22 条
[1]   Halovinyl aldehydes: useful tools in organic synthesis [J].
Brahma, Sulagna ;
Ray, Jayanta K. .
TETRAHEDRON, 2008, 64 (13) :2883-2896
[2]  
Ciganek E., 1984, ORG REACT, V32, P1, DOI DOI 10.1002/0471264180.OR032.01
[3]  
Claeys S, 2002, EUR J ORG CHEM, V2002, P1051
[4]   Synthetic and Theoretical Investigations on the Construction of Oxanorbornenes by a Michael Addition and Intramolecular Diels-Alder Furan Reaction [J].
Dadwal, Mamta ;
Kesharwani, Manoj K. ;
Danayak, Vaishalee ;
Ganguly, Bishwajit ;
Mobin, Shaikh M. ;
Muruganantham, Rajendran ;
Namboothiri, Irishi N. N. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (36) :6106-6118
[5]   Modern methods for the synthesis of substituted naphthalenes [J].
de Koning, CB ;
Rousseau, AL ;
van Otterlo, WAL .
TETRAHEDRON, 2003, 59 (01) :7-36
[6]   The intramolecular Diels-Alder reactions of photochemically generated trans-cycloalkenones [J].
Dorr, H ;
Rawal, VH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :10229-10230
[7]   TRIMETHYLSILYL CYANIDE - A REAGENT FOR UMPOLUNG - FURFURAL, A CONVENIENT PRECURSOR FOR INTRAMOLECULAR DIELS-ALDER REACTIONS VIA UMPOLUNG WITH TRIMETHYLSILYL CYANIDE [J].
FISCHER, K ;
HUNIG, S .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04) :564-569
[8]   Coupling of Fischer carbene complexes with conjugated enyne-aldehydes and ketones: A novel synthesis of furan derivatives [J].
Herndon, JW ;
Wang, HX .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (14) :4564-4565
[9]   Intramolecular Diels-Alder reactions of optically active allenic ketones: Chirality transfer in the preparation of substituted oxa-bridged octalones [J].
Jung, ME ;
Min, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (31) :10834-10835
[10]   GEM-DIALKYL EFFECT IN THE INTRAMOLECULAR DIELS-ALDER REACTION OF 2-FURFURYL METHYL FUMARATES - THE REACTIVE ROTAMER EFFECT, ENTHALPIC BASIS FOR ACCELERATION, AND EVIDENCE FOR A POLAR TRANSITION-STATE [J].
JUNG, ME ;
GERVAY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :224-232