Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2007(13): 2050-2054
DOI: 10.1055/s-2007-983739
DOI: 10.1055/s-2007-983739
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Platinum- and Ruthenium-Catalyzed Aromatization of Enediynes via Intramolecular Nucleophilic Additions
Further Information
Received
1 April 2007
Publication Date:
26 June 2007 (online)
Publication History
Publication Date:
26 June 2007 (online)
Abstract
Catalytic cyclization of enediynes via intramolecular nucleophilic addition was achieved with TpRuPPh3(MeCN)2PF6 and platinum dichloride, giving naphthalene-fused 2,3-dihydrofurans and -pyrroles in good yields. On the basis of experimental results, the mechanism is proposed to involve nucleophilic addition to a π-alkyne intermediate, followed by alkyne insertion.
Key words
enediynes - aromatization - intramolecular nucleophilic addition - ruthenium - platinum
-
1a
Bergman RG. Acc. Chem. Res. 1973, 6: 25 -
1b
Lockhart TP.Comita PB.Bergman RG. J. Am. Chem. Soc. 1981, 103: 4082 - Reviews:
-
2a
Enediyne Antibiotics as Antitumor Agents
Borders DB.Doyle TW. Marcel Dekker; New York: 1995. -
2b
Xi Z.Goldberg IH. In Comprehensive Natural Product Chemistry Vol. 7:Barton DHR.Nakanishi K. Pergamon; Oxford: 1999. p.553 - Recent reviews:
-
3a
Basak A.Mandal S.Bag SS. Chem. Rev. 2003, 103: 4077 -
3b
Rawat DS.Zaleski JM. Synlett 2004, 393 -
3c
Bowles DM.Palmer GJ.Landis CA.Scott JL.Anthony JE. Tetrahedron 2001, 57: 3753 -
3d
Grissom JW.Gunawardena GU.Klingberg D.Huang D. Tetrahedron 1996, 52: 6453 -
3e
Wang KK. Chem. Rev. 1996, 96: 207 - For selected examples of stoichiometric metal-mediated Bergman cyclizations, see:
-
4a
Wang YS.Finn MG. J. Am. Chem. Soc. 1995, 117: 8045 -
4b
O’Connor JM.Friese SJ.Tichenor M. J. Am. Chem. Soc. 2002, 124: 3506 -
4c
Zaleski JM.Rawat DS. J. Am. Chem. Soc. 2001, 123: 9675 -
4d
Warner BP.Millar SP.Broene RD.Buchwald SL. Science 1995, 269: 814 -
4e
Konig B.Hollnagel H.Ahrens B.Jones PG. Angew. Chem., Int. Ed. Engl. 1995, 34: 2538 -
4f
Landis CA.Payne MM.Eaton DL.Anthony JE. J. Am. Chem. Soc. 2004, 126: 1338 - 5
Odedra A.Wu C.-J.Pratap BP.Huang C.-W.Ran Y.-F.Liu R.-S. J. Am. Chem. Soc. 2005, 127: 3406 - For the PtCl2/CO system, see
-
6a
Fürstner A.Davies PW.Gress T. J. Am. Chem. Soc. 2005, 127: 8244 -
6b
Fürstner A.Aïssa C. J. Am. Chem. Soc. 2006, 128: 6306 -
6c
Fürstner A.Davies PW. J. Am. Chem. Soc. 2005, 127: 15024 - 7
Taduri BP.Ran Y.-F.Huang C.-W.Liu R.-S. Org. Lett. 2006, 8: 883 - 8
Chan W.-C.Lau C.-P.Chan Y.-Z.Fang Y.-Q.Ng S.-M.Jia G. Organometallics 1997, 16: 34