Fused tetracycles with a benzene or cyclohexadiene core: [2+2+2] cycloadditions on macrocyclic systems

被引:29
作者
Brun, Sandra [1 ]
Garcia, Lidia [1 ]
Gonzalez, Ivan [1 ]
Torrent, Anna [1 ]
Dachs, Anna [1 ]
Pla-Quintana, Anna [1 ]
Parella, Teodor [2 ]
Roglans, Anna [1 ]
机构
[1] Univ Girona, Dept Chem, E-17071 Girona, Spain
[2] Univ Autonoma Barcelona, Servei RMN, E-08193 Barcelona, Spain
关键词
D O I
10.1039/b806524a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of fused tetracycles with a benzene or cyclohexadiene core (2a-h) is satisfactorily prepared by intramolecular [2 + 2 + 2] cycloadditions of triynic and enediynic macrocycles (1a-h) under RhCl(PPh3)(3) catalysis; the enantioselective cycloaddition of macrocycles 1b and le gives chiral tetracycles with moderate enantiomeric excess.
引用
收藏
页码:4339 / 4341
页数:3
相关论文
共 34 条
[1]   Modified synthesis of heptahelicene and its resolution into single enantiomers [J].
Alexandrova, Zuzana ;
Sehnal, Petr ;
Stara, Irena G. ;
Stary, Ivo ;
Saman, David ;
Urquhart, Stephen G. ;
Otero, Edwige .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2006, 71 (08) :1256-1264
[2]   Redox modulation of benzene triimides and diimides via noncovalent interactions [J].
Carroll, JB ;
Gray, M ;
McMenimen, KA ;
Hamilton, DG ;
Rotello, VM .
ORGANIC LETTERS, 2003, 5 (18) :3177-3180
[3]   Novel C3v-Symmetric tripodal scaffold, triethyl cis,cis,cis-2,5,8-tribenzyltrindane-2,5,8-tricarboxylate, for the construction of artificial receptors [J].
Choi, HJ ;
Park, YS ;
Yun, SH ;
Kim, HS ;
Cho, CS ;
Ko, K ;
Ahn, KH .
ORGANIC LETTERS, 2002, 4 (05) :795-798
[4]   [2+2+2] cycloaddition reactions catalyzed by transition metal complexes [J].
Chopade, Pramod R. ;
Louie, Janis .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2307-2327
[5]   Recent progress in cobalt-mediated [2+2+2] cycloaddition reactions [J].
Gandon, Vincent ;
Aubert, Corinne ;
Malacria, Max .
CHEMICAL COMMUNICATIONS, 2006, (21) :2209-2217
[6]   Palladium and rhodium-catalyzed intramolecular [2+2+2] cycloisomerizations in molten tetrabutylammonium bromide [J].
Gonzalez, Ivan ;
Bouquillon, Sandrine ;
Roglans, Anna ;
Muzart, Jacques .
TETRAHEDRON LETTERS, 2007, 48 (37) :6425-6428
[7]   Metal complexes of trindane: Possible precursors of sumanene [J].
Gupta, HK ;
Lock, PE ;
McGlinchey, MJ .
ORGANOMETALLICS, 1997, 16 (16) :3628-3634
[8]   Exchange reactions in aluminosilicate solutions [J].
Harris, RK ;
Parkinson, J ;
SamadiMaybodi, A ;
Smith, W .
CHEMICAL COMMUNICATIONS, 1996, (05) :593-594
[9]   The incorporation of aluminum into silicate ions in alkaline aqueous solutions, studied by aluminum-27 nmr [J].
Harris, RK ;
SamadiMaybodi, A ;
Smith, W .
ZEOLITES, 1997, 19 (2-3) :147-155
[10]   Transition metal catalyzed [2+2+2] cycloaddition and application in organic synthesis [J].
Kotha, S ;
Brahmachary, E ;
Lahiri, K .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (22) :4741-4767