Reaction of α-Ene-Vinylcyclopropanes: Type II Intramolecular [5+2] Cycloaddition or [3+2] Cycloaddition?

被引:68
作者
Li, Qian [1 ]
Jiang, Guo-Jie [1 ]
Jiao, Lei [1 ]
Yu, Zhi-Xiang [1 ]
机构
[1] Peking Univ, BNLMS, Key Lab Bioorgan Chem & Mol Engn, Coll Chem, Beijing 100871, Peoples R China
关键词
ASYMMETRIC TOTAL-SYNTHESIS; RING-SYSTEMS; METAL; ALLENES; CYCLOISOMERIZATION; REARRANGEMENTS; SELECTIVITY; ROUTE; 1ST;
D O I
10.1021/ol100237h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Exposure of alpha-ene-VCPs to catalytic [Rh(dppm)]SbF6 led to the discovery of a novel Rh(I)-catalyzed [3+2] reaction, which was shown to be efficient for the construction of 5/6- and 5/7-bicyclic compounds rather than the anticipated type II [5+2] products.
引用
收藏
页码:1332 / 1335
页数:4
相关论文
共 36 条
[1]   Enantioselective syntheses of tremulenediol A and tremulenolide A [J].
Ashfeld, BL ;
Martin, SF .
ORGANIC LETTERS, 2005, 7 (20) :4535-4537
[2]  
Bear BR, 2001, ANGEW CHEM INT EDIT, V40, P821
[3]  
BERTRAND MP, 1994, SYNLETT, P736
[4]   A general synthetic route to differentially functionalized angularly and linearly fused [6-7-5] ring systems: A Rh(I)-catalyzed cyclocarbonylation reaction [J].
Brummond, Kay A. ;
Chen, Daitao ;
Davis, Matthew A. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) :5064-5068
[5]   Mo(CO)6- and [Rh(CO)2Cl]2-catalyzed allenic cyclocarbonylation reactions of alkynones:: Efficient access to bicyclic dienediones [J].
Brummond, Kay M. ;
Chen, Daitao .
ORGANIC LETTERS, 2008, 10 (05) :705-708
[6]   FREE RADICAL-MEDIATED RING EXPANSION AND RELATED ANNULATIONS [J].
DOWD, P ;
ZHANG, W .
CHEMICAL REVIEWS, 1993, 93 (06) :2091-2115
[7]   A cheap metal for a "Noble" task:: Preparative and mechanistic aspects of cycloisomerization and cycloaddition reactions catalyzed by low-valent iron complexes [J].
Fuerstner, Alois ;
Majima, Keisuke ;
Martin, Ruben ;
Krause, Helga ;
Kattnig, Egmont ;
Goddard, Richard ;
Lehmann, Christian W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (06) :1992-2004
[8]   Rhodium(I)-catalyzed intramolecular Pauson-Khand-type [2+2+1] cycloaddition of allenenes [J].
Inagaki, F ;
Mukai, C .
ORGANIC LETTERS, 2006, 8 (06) :1217-1220
[9]   Rhodium(I)-Catalyzed Intramolecular Carbonylative [2+2+1] Cycloaddition of Bis(allene)s: Bicyclo[6.3.0]undecadienones and Bicyclo[5.3.0]decadienones [J].
Inagaki, Fuyuhiko ;
Narita, Syu ;
Hasegawa, Takuma ;
Kitagaki, Shinji ;
Mukai, Chisato .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (11) :2007-2011
[10]   Rh(I)-catalyzed Intramolecular [3+2] cycloaddition of trans-vinylcycloproplane-enes [J].
Jiao, Lei ;
Ye, Siyu ;
Yu, Zhi-Xiang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) :7178-+