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Synthesis 2004(14): 2411-2417
DOI: 10.1055/s-2004-829189
DOI: 10.1055/s-2004-829189
PSP
© Georg Thieme Verlag Stuttgart · New York
Stereoselective Synthesis and Reactivity of Dienyl Zirconocene Derivatives
Further Information
Received
26 April 2004
Publication Date:
30 July 2004 (online)
Publication History
Publication Date:
30 July 2004 (online)
Abstract
Stereoselective dienyl zirconocene derivatives have been prepared via a tandem allylic C-H bond activation isomerization-elimination reaction. These reagents can be either trapped directly with electrophiles or transmetalated to copper to participate in several carbon-carbon bond formations. When the transmetalation is performed on allylic as well as vinylic zirconocene derivatives, the reaction occurs with inversion of stereochemistry of the dienyl system.
Key words
zirconocene - dienyls - transmetalation - isomerization
- For reviews see:
-
1a
Marek I. J. Chem. Soc., Perkin Trans. 1 1999, 535 -
1b
Marek I. In Modern C,C- and C,X-Bond Formations by Metal-Catalyzed Cross-Coupling Reactionsde Meijere A.Diederich F. Wiley-VCH; Weinheim, Germany: 2004. p.in press -
1c
Marek I. In Transition Metals for Organic Synthesis 2nd ed.:Beller M.Bolm C. Wiley-VCH; Weinheim, Germany: 2004. p.in press -
1d
Marek I.Normant JF. In Metal-Catalyzed Cross Coupling ReactionsDiederich F.Stang PJ. Wiley-VCH; Weinheim, Germany: 1998. p.271 -
1e
Normant JF.Alexakis A. Synthesis 1981, 841 -
1f
Knochel P. In Comprehensive Organic Synthesis Vol. 4:Trost BM.Fleming I.Semmelhack MF. Pergamon Press; New York: 1991. p.865 -
1g
Negishi E. Pure Appl. Chem. 1981, 53: 2333 -
1h
Fallis AG.Forgione P. Tetrahedron 2001, 57: 5899 -
2a
Forgione P.Wilson PD.Fallis AG. Tetrahedron Lett. 2000, 41: 17 -
2b
Forgione P.Wilson PD.Yap GPA.Fallis AG. Synthesis 2000, 921 -
2c
Alexakis A.Normant JF. Tetrahedron Lett. 1982, 23: 5151 -
2d
Furber M.Taylor RJK.Burford SC. J. Chem. Soc., Perkin Trans 1 1986, 1809 - 3
Negishi E. In Titanium and Zirconium in Organic SynthesisMarek I. VCH; Weinheim, Germany: 2002. p.1 - 4
Liard A.Marek I. J. Org. Chem. 2000, 65: 7218 - 5
Farhat S.Marek I. Angew. Chem. Int. Ed. 2002, 41: 1410 -
6a
Liard A.Chechik H.Farhat S.Morlender-Vais N.Averbuj C.Marek I. J. Organomet. Chem. 2001, 624: 26 -
6b
Chinkov N.Chechik H.Majumdar S.Marek I. Synthesis 2002, 2473 -
7a
Swanson DR.Negishi E. Organometallics 1991, 10: 825 -
7b
Maye JP.Negishi E. Tetrahedron Lett. 1993, 34: 3359 -
7c
Negishi E.Maye JP.Choueiry D. Tetrahedron 1995, 51: 4447 -
8a
Chinkov N.Majumdar S.Marek I. J. Am. Chem. Soc. 2002, 124: 10282 -
8b
Chinkov N.Majumdar S.Marek I. J. Am. Chem. Soc. 2003, 125: 13258 - 9
Alexakis A.Normant JF. Isr. J. Chem. 1984, 24: 113 -
10a
Cuvigny T.Herve du Penhoat C.Julia M. Tetrahedron 1986, 42: 5329 -
10b
Backvall JE.Chinchilla R.Najera C.Yus M. Chem. Rev. 1998, 98: 2291 -
11a
Mintz EA.Ward AS.Tice DS. Organometallics 1985, 4: 1308 -
11b
Ward AS.Mintz EA.Kramer MP. Organometallics 1988, 7: 8 - 12
Rozema MJ.Knochel P. Tetrahedron Lett. 1991, 32: 185 -
13a
Nakamura E.Kuwajima I. J. Am. Chem. Soc. 1984, 106: 3368 -
13b
Corey EJ.Boaz NW. Tetrahedron Lett. 1985, 26: 6015 -
13c
Alexakis A.Berlan J.Besace Y. Tetrahedron Lett. 1986, 27: 2143