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Synthesis 2010(21): 3649-3656
DOI: 10.1055/s-0030-1258227
DOI: 10.1055/s-0030-1258227
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Trapping the π-Allylpalladium Intermediate from Fulvene-Derived Azabicyclic Olefin with Soft Nucleophiles
Further Information
Received
17 June 2010
Publication Date:
25 August 2010 (online)
Publication History
Publication Date:
25 August 2010 (online)
Abstract
A facile method for the synthesis of a new class of disubstituted alkylidenecyclopentenes has been introduced. The methodology involves the palladium-catalyzed ring opening of pentafulvene-derived bicyclic hydrazines with phenols and active methylene compounds, furnishing 1,4-disubstituted alkylidenecyclopentenes in good yield. The utility of multiple points of functionalization was effectively demonstrated by the synthesis of a substituted cyclopentanone and 2-hydrazinofulvene.
Key words
azabicyclic olefin - palladium - soft nucleophile - alkylidenecyclopentene - substituted cyclopentanone - 2-hydrazinofulvene
- 1
Hudlicky T.Price JD. Chem. Rev. 1989, 89: 1467 -
2a
Storsberg J.Nandakumar MV.Sankaranarayanan S.Kaufmann DE. Adv. Synth. Catal. 2001, 343: 177 -
2b
Yao M.-L.Adiwidjaja G.Kaufmann DE. Angew. Chem. Int. Ed. 2002, 41: 3375 -
2c
Pineschi M.Moro FD.Crotti P.Macchia F. Org. Lett. 2005, 7: 3605 -
2d
Bournaud C.Falciola C.Lecourt T.Rosset S.Alexakis A.Micouin L. Org. Lett. 2006, 8: 3581 -
2e
Radhakrishnan KV.Sajisha VS.Anas S.Krishnan KS. Synlett 2005, 2273 -
2f
Sajisha VS.Mohanlal S.Anas S.Radhakrishnan KV. Tetrahedron 2006, 62: 3997 -
2g
Sajisha VS.Radhakrishnan KV. Adv. Synth. Catal. 2006, 348: 924 -
2h
John J.Adarsh B.Radhakrishnan KV. Tetrahedron 2010, 66: 1383 - 3
Bian J.Wingerden MV.Ready JM. J. Am. Chem. Soc. 2006, 128: 7428 - 4
Brady SF.Singh MP.Janso J.Clardy J. J. Am. Chem. Soc. 2000, 122: 2116 - 5
Trost BM.Dong L.Schroeder GM. J. Am. Chem. Soc. 2005, 127: 10259 -
6a
Trost BM.Chan DMT. J. Am. Chem. Soc. 1979, 101: 6429 -
6b
Trost BM.Chan DMT. J. Am. Chem. Soc. 1979, 101: 6432 -
7a
Yamamoto Y.Ohkoshi N.Kameda M.Itoh K. J. Org. Chem. 1999, 64: 2178 -
7b
Binder JT.Crone B.Haug TT.Menz H.Kirsch SF. Org. Lett. 2008, 10: 1025 -
7c
Oestreich M.Frohlich R.Hoppe D. J. Org. Chem. 1999, 64: 8616 -
7d
Marco-Contelles J.Rodriguez M. Tetrahedron Lett. 1998, 39: 6749 -
7e
Ballini R.Bosica G.Florini D.Victoria M.Petrini M. Org. Lett. 2001, 3: 1265 - 8
Hayashi M.Ohmatsu T.Meng YP.Saigo K. Angew Chem. Int. Ed. 1998, 37: 837 - 9
Corkey BK.Toste FD. J. Am. Chem. Soc. 2005, 127: 17168 -
10a
Barluenga J.Vicente R.Barrio P.Lopez LA.Tomas M. J. Am. Chem. Soc. 2004, 126: 5974 -
10b
Barluenga J.Vicente R.Barrio P.Lopez LA.Tomas M. J. Am. Chem. Soc. 2006, 128: 7050 - 11
Tang X.-Y.Shi M. J. Org. Chem. 2010, 75: 902 - 12
Anas S.Sajisha VS.Mohanlal S.Radhakrishnan KV. Synlett 2006, 2399 - 13
Anas S.John J.Sajisha VS.John J.Rajan R.Suresh E.Radhakrishnan KV. Org. Biomol. Chem. 2007, 5: 4010 - 14
Anas S.Sajisha VS.John J.Joseph N.George SC.Radhakrishnan KV. Tetrahedron 2008, 64: 9689 - 15
Luna AP.Cesario M.Bonin M.Micouin L. Org. Lett. 2003, 5: 4771 - 16
Hand
Book of Organopalladium Chemistry for Organic Synthesis
Vol.
2:
Negishi E. Wiley-Interscience; New York: 2002.