Palladium/Lewis acid catalyzed desymmetrization of fulvene-derived bicyclic hydrazines: A facile synthesis of substituted alkylidene cyclopentenes

被引:18
作者
Anas, S. [1 ]
Sajisha, V. S. [1 ]
Mohanlal, Smitha [1 ]
Radhakrishnan, K. V. [1 ]
机构
[1] CSIR, Reg Res Lab, Organ Chem Sect, Chem Sci & Technol Div, Trivandrum 695019, Kerala, India
关键词
fulvenes; bicyclic hydrazines; alkylidene cyclopentenes; organostarmanes; Lewis acids;
D O I
10.1055/s-2006-950402
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Desymmetrization of fulvene-derived bicyclic hydrazines by a palladium/Lewis acid catalyzed reaction with allyl and vinyl stannanes leading to the efficient synthesis of synthetically important alkylidene cyclopentenes is described.
引用
收藏
页码:2399 / 2402
页数:4
相关论文
共 38 条
[1]   Highly chemo-, regio-, and stereoselective [3+2]-cyclization of activated and deactivated allenes with alkenyl Fischer carbene complexes:: A straightforward access to alkylidenecyclopentanone derivatives [J].
Barluenga, Jose ;
Vicente, Ruben ;
Lopez, Luis A. ;
Tomas, Miguel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :7050-7054
[2]   Enantioselective total synthesis of (+)- and (-)-nigellamine A2 [J].
Bian, Jianwei ;
Van Wingerden, Matthew ;
Ready, Joseph M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) :7428-7429
[3]   Guanacastepene, a fungal-derived diterpene antibiotic with a new carbon skeleton [J].
Brady, SF ;
Singh, MP ;
Janso, JE ;
Clardy, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (09) :2116-2117
[4]   Atom transfer reactions of TMM diyls directed toward the synthesis of rudmollin [J].
Carroll, GL ;
Allan, AK ;
Schwaebe, MK ;
Little, RD .
ORGANIC LETTERS, 2000, 2 (16) :2531-2534
[5]   A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol [J].
Du, YS ;
Lu, XY .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6463-6465
[6]   SYNTHESIS OF RODLIKE DISTELLENES [J].
GLEITER, R ;
BORZYK, O .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (09) :1001-1003
[7]   AMINOCYCLOPENTITOLS FROM FULVENES - SYNTHESES OF (+)-TREHAZOLIN AND THE PENTASUBSTITUTED CYCLOPENTANE OF KERUFFARIDE [J].
GOERING, BK ;
LI, J ;
GANEM, B .
TETRAHEDRON LETTERS, 1995, 36 (49) :8905-8908
[8]   CYCLOPENTENONE DERIVATIVES .6. 4-OXO-2-CYCLOPENTENYL ACETATE - A SYNTHETIC INTERMEDIATE [J].
HARRE, M ;
RADDATZ, P ;
WALENTA, R ;
WINTERFELDT, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (07) :480-492
[9]   [3+2] Annulation of allylidenetriphenylphosphorane with 1,2-diacylethylenes and 1,2-diacylacetylenes: A one-step synthesis of tri- and tetrasubstituted cyclopentadienes and fulvenes [J].
Himeda, Y ;
Yamataka, H ;
Ueda, I ;
Hatanaka, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6529-6538
[10]   Intramolecular Diels-Alder cycloadditions of fulvenes. Application to the kigelinol, neoamphilectane, and kempane skeletons [J].
Hong, BC ;
Chen, FL ;
Chen, SH ;
Liao, JH ;
Lee, GH .
ORGANIC LETTERS, 2005, 7 (04) :557-560