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Synthesis 2004(7): 1115-1118
DOI: 10.1055/s-2004-815971
DOI: 10.1055/s-2004-815971
PSP
© Georg Thieme Verlag Stuttgart · New YorkReductive Ring Opening of Oxygen-Containing Benzo-Fused Heterocycles by an Arene-Catalysed Lithiation
Further Information
Received
29 December 2003
Publication Date:
12 February 2004 (online)
Publication History
Publication Date:
12 February 2004 (online)
Abstract
The reductive ring opening of phthalan and isochroman in a 8 mmol scale process, using a small excess of lithium (1.35 equiv) and a substoichiometric amount of DTBB (3 mol%), leads to functionalised organolithium compounds, which after reaction with (-)-menthone as electrophile followed by hydrolysis with water, gives the corresponding diols in good yields with high stereoselectivity. Dehydration of these diols leads to the corresponding oxygen-containing heterocycles, which are homologous of the starting heterocycles.
Key words
functionalised organolithium compounds - stereoselective addition - reductive opening - lithiation
- For reviews, see:
- 1a
Nájera C.Yus M. Trends Org. Chem. 1991, 2: 155 - 1b
Nájera C.Yus M. Recent Res. Dev. Org. Chem. 1997, 1: 67 - 1c
Nájera C.Yus M. Curr. Org. Chem. 2003, 7: 867 - 2a
Wakefield B. Organolithium Methods Academic Press; London: 1988. - 2b
Clayden J. Organolithiums: Selectivity for Synthesis Pergamon; Amsterdam: 2002. - For reviews, see:
- 3a
Yus M.Foubelo F. Rev. Heteroatom Chem. 1997, 17: 73 - 3b
Yus M.Foubelo F. Targets in Heterocyclic Systems 2002, 6: 136 - 3c
Yus M. Pure Appl. Chem. 2003, 75: 1453 - 4a
Alonso F.Lorenzo E.Yus M. Tetrahedron Lett. 1997, 38: 2187 - 4b
Sabes SF.Urbanek RA.Forsyth CJ. J. Am. Chem. Soc. 1998, 120: 2534 - 4c
Alonso F.Lorenzo E.Yus M. Tetrahedron Lett. 1998, 39: 3303 - 4d
Lorenzo E.Alonso F.Yus M. Tetrahedron 2000, 56: 1745 - 4e
Lorenzo E.Alonso F.Yus M. Tetrahedron Lett. 2000, 41: 1661 - 4f
Alonso F.Falvello LR.Fanwick PE.Lorenzo E.Yus M. Synthesis 2000, 949 - 4g
Alonso F.Meléndez J.Yus M. Helv. Chim. Acta 2002, 85: 3262 - 4h
Yus M.Maciá B.Gómez C. Tetrahedron 2003, 59: 5183 - 4i
Alonso F.Lorenzo E.Meléndez J.Yus M. Tetrahedron 2003, 59: 5199 - 5a
Azzena U.Demartis S.Fiori MG.Melloni G.Pisano L. Tetrahedron Lett. 1995, 36: 5641 - 5b
Almena J.Foubelo F.Yus M. J. Org. Chem. 1996, 61: 1859 - 5c
Almena J.Foubelo F.Yus M. Tetrahedron 1996, 52: 8545 - 5d For a review, see:
Azzena U. Trends Org. Chem. 1997, 6: 55 - 5e
Almena J.Foubelo F.Yus M. Tetrahedron 1997, 53: 5563 - 5f
Azzena U.Carta S.Melloni G.Sechi A. Tetrahedron 1997, 53: 16205 - 6a
Maercker A. Angew. Chem., Int. Ed. Engl. 1987, 26: 972 - 6b
Lazana MCRLR.Franco MLTMB.Herold BJ. J. Am. Chem. Soc. 1989, 111: 8640 - 6c
Casado F.Pisano L.Farriol M.Gallardo I.Marquet J.Melloni G. J. Org. Chem. 2000, 65: 322 - 6d
Azzena U.Denurra T.Melloni G.Piroddi AM. J. Org. Chem. 1990, 55: 5386 - 6e
Azzena U.Denurra T.Melloni G.Fenude E.Rassu G. J. Org. Chem. 1992, 57: 1444 - 6f
Bachki A.Foubelo F.Yus M. Tetrahedron Lett. 1998, 39: 7759 - 6g
Foubelo F.Yus M. Tetrahedron Lett. 1999, 40: 743 - 6h
Foubelo F.Saleh SA.Yus M. J. Org. Chem. 2000, 65: 3478 - 6i
Ferrández JV.Foubelo F.Yus M. Eur. J. Org. Chem. 2001, 3223 - 6j
Yus M.Foubelo F.Ferrández JV.Bachki A. Tetrahedron 2002, 58: 4907 - 7a
Screttas CG.Micha-Screttas M. J. Org. Chem. 1978, 43: 1064 - 7b
Screttas CG.Micha-Screttas M. J. Org. Chem. 1979, 44: 713 - 7c
Cohen T.Bhupathy M. Acc. Chem. Res. 1989, 22: 152 - 7d
Foubelo F.Gutiérrez A.Yus M. Tetrahedron Lett. 1997, 38: 4837 - 7e
Foubelo F.Gutiérrez A.Yus M. Synthesis 1999, 503 - 7f
Foubelo F.Gutiérrez A.Yus M. Tetrahedron Lett. 1999, 40: 8173 - 7g
Foubelo F.Gutiérrez A.Yus M. Tetrahedron Lett. 1999, 40: 8177 - 7h
Foubelo F.Yus M. Tetrahedron Lett. 2000, 41: 5335 - 7i
Gutiérrez A.Foubelo A.Yus M. Tetrahedron 2001, 57: 4411 - 7j
Yus M.Foubelo F.Ferrández JV. Chem. Lett. 2002, 726 - 7k
Yus M.Foubelo F.Ferrández JV. Tetrahedron Lett. 2002, 43: 7205 - 7l
Yus M.Foubelo F.Ferrández JV. Tetrahedron 2003, 59: 2083 - 8 For the first account of this reaction, see:
Yus M.Ramón DJ. J. Chem. Soc., Chem. Commun. 1991, 398 - For reviews, see:
- 9a
Yus M. Chem. Soc. Rev. 1996, 155 - 9b
Ramón DJ.Yus M. Eur. J. Org. Chem. 2000, 225 - 9c
Yus M. Synlett 2001, 1197 - 10a
Gómez C.Ruiz S.Yus M. Tetrahedron Lett. 1998, 39: 1397 - 10b
Gómez C.Ruiz S.Yus M. Tetrahedron 1999, 55: 7017 - 11
Yus M.Gómez C.Candela P. Tetrahedron 2002, 58: 6207 - For studies on the mechanism of this reaction, see:
- 12a
Yus M.Herrera RP.Guijarro A. Tetrahedron Lett. 2001, 42: 3455 - 12b
Yus M.Herrera RP.Guijarro A. Chem.-Eur. J. 2002, 8: 2574 - 12c
Herrera RP.Guijarro A.Yus M. Tetrahedron Lett. 2003, 44: 1309 - 12d
Herrera RP.Guijarro A.Yus M. Tetrahedron Lett. 2003, 44: 1313 - 13
Almena J.Foubelo F.Yus M. Tetrahedron 1995, 51: 3351 - 14
Almena J.Foubelo F.Yus M. Tetrahedron 1995, 51: 3365 - 15a
Soler T.Bachki A.Falvello LR.Foubelo F.Yus M. Tetrahedron: Asymmetry 1998, 9: 3939 - 15b
Soler T.Bachki A.Falvello LR.Foubelo F.Yus M. Tetrahedron: Asymmetry 2000, 11: 493 - 16a
Falvello LR.Foubelo F.Soler T.Yus M. Tetrahedron: Asymmetry 2000, 11: 2063 - 16b
Foubelo F.Soler T.Yus M. Tetrahedron: Asymmetry 2001, 12: 801 - 17
Yus M.Gomis J. Eur. J. Org. Chem. 2003, 2043 - 18
Pastor IM.Yus M. Tetrahedron Lett. 2000, 41: 1589 - 19
Pastor IM.Yus M. Tetrahedron 2001, 57: 2371 - 20
Yus M.Gomis J. Tetrahedron Lett. 2001, 42: 5721 - 21
Yus M.Gomis J. Eur. J. Org. Chem. 2002, 1989 - 22
Yus M.Gomis J. Tetrahedron 2003, 59: 4967