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Synlett 2008(7): 1071-1075
DOI: 10.1055/s-2008-1042919
DOI: 10.1055/s-2008-1042919
LETTER
© Georg Thieme Verlag Stuttgart · New York
Tandem [2+1] Cycloaddition-Ring Expansion of Bicyclic Alkenes with Tertiary Propargylic Acetates Catalyzed by Palladium(II)-Coordinated Phosphinous Acid
Weitere Informationen
Received
22 December 2007
Publikationsdatum:
17. März 2008 (online)
Publikationsverlauf
Publikationsdatum:
17. März 2008 (online)
Abstract
Palladium-SPO complex catalyzed the tandem [2+1] cycloaddition-ring expansion of norbornene derivatives with tertiary propargylic acetates to afford bicyclo[3.2.1]octadienes.
Key words
palladium - secondary phosphine oxides - tertiary propargylic acetate - bicyclic alkene - tandem reaction
-
1a
Roudhill DM.Sperline RP.Beaulieu WB. Coord. Chem. Rev. 1978, 26: 263 -
1b
Walther B. Coord. Chem. Rev. 1984, 60: 67 -
1c
Appleby T.Woollins JD. Coord. Chem. Rev. 2002, 235: 121 - For reviews, see:
-
2a
Ackermann L. Synthesis 2006, 1557 -
2b
Dubrovina NV.Börner A. Angew. Chem. Int. Ed. 2004, 43: 5883 -
3a
Li GY.Zheng G.Noonan AF. J. Org. Chem. 2001, 66: 8677 -
3b
Li GY. Angew. Chem. Int. Ed. 2001, 40: 1513 -
3c
Li GY.Fagan PJ.Watson PL. Angew. Chem. Int. Ed. 2001, 40: 1106 - 4 For a review, see:
Ackermann L.Born R.Spatz JH.Althammer A.Gschrei CJ. Pure Appl. Chem. 2006, 78: 209 - 5
Nemoto T.Matsuda T.Akimoto Y.Fukuyama T.Hamada Y. Org. Lett. 2005, 7: 4447 -
6a
Dai W.-M.Yeung KKY.Leung WH.Haynes RK. Tetrahedron: Asymmetry 2003, 14: 2821 -
6b
Nemoto T.Matsumoto T.Matsuda T.Hitomi T.Hatano K.Hamada Y. J. Am. Chem. Soc. 2004, 126: 3690 -
6c
Nemoto T.Matsuda T.Matsumoto T.Hamada Y. J. Org. Chem. 2005, 70: 7172 - 7
Jiang X.Minnaard AJ.Hessen B.Feringa BL.Duchateau ALL.Andrien JGO.Boogers JAF.de Vries JG. Org. Lett. 2003, 5: 1503 - 8
Jiang X.van den Berg M.Minnaard AJ.Feringa BL.de Vries JG. Tetrahedron: Asymmetry 2004, 15: 2223 - 9
Lerebour R.Wolf C. Org. Lett. 2007, 9: 2737 - 10
Bigeault J.Giordano L.Buono G. Angew. Chem. Int. Ed. 2005, 44: 4753 - 11
Bigeault J.Giordano L.de Riggi I.Gimbert Y.Buono G. Org. Lett. 2007, 9: 3567 - 12
Goering HL.Kantner SS. J. Org. Chem. 1984, 49: 422 -
13a
See ref. 10, 11.
-
13b
Tenaglia A.Giordano L.Buono G. Org. Lett. 2006, 8: 4315 - 15 For a similar observation, see:
Lautens M.Fagnou K.Yang D. J. Am. Chem. Soc. 2003, 125: 14884 - 16 For a similar proposed mechanism with TiCl4 as Lewis acid, see:
Huang X.Su C.Liu Q.Song Y. Synlett 2008, 229 - 17 The exo selectivity for the nucleophilic attack of the acetate is well established. See:
Battiste MA.Coxon JM.Edelman R. Tetrahedron Lett. 1972, 45: 4577 - For the formation of HPd(OAc)(PPh3)2, see:
-
18a
Trost B.Rise F. J. Am. Chem. Soc. 1987, 109: 3161 -
18b
Trost B.Schmidt T. J. Am. Chem. Soc. 1988, 110: 2301 - 19 For a recent example concerning the Pd(0)-catalyzed reaction of vinylidenecyclopropanes with acetic acid, see:
Lu J.-M.Shi M. Tetrahedron 2006, 62: 9115 - For the enantioselective synthesis of SPO, see:
-
20a
Leyris A.Nuel D.Giordano L.Achard M.Buono G. Tetrahedron Lett. 2005, 46: 8673 -
20b
Leyris A.Bigeault J.Nuel D.Giordano L.Buono G. Tetrahedron Lett. 2007, 48: 5247
References and Notes
Reaction carried out without Pd(OAc)2/CyPhP(O)H as a catalytic system did not proceed at all.