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Synlett 2004(1): 119-121
DOI: 10.1055/s-2003-43369
DOI: 10.1055/s-2003-43369
LETTER
© Georg Thieme Verlag Stuttgart · New York
On the Formation of β-Hydroxy-dihydropyrroles from Metal-Catalysed Cyclisations of γ-Ynyl-β-hydroxy-α-amino Esters
Weitere Informationen
Received
27 October 2003
Publikationsdatum:
26. November 2003 (online)
Publikationsverlauf
Publikationsdatum:
26. November 2003 (online)
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Abstract
Copper(I), palladium(II) and mercury(II) salts in hot Et2O-pyridine mixtures can all induce 5-endo-dig cyclisations of the anti-γ-ynyl-β-hydroxy-α-amino esters 7 to give good yields of the hydroxy-dihydropyrroles 9 and subsequently the related pyrroles 8, following elimination; of the salts tested, copper(I) acetate proved to be the reagent of choice.
Key words
β-hydroxy-dihydropyrroles - γ-ynyl-β-hydroxy-α-amino esters - metal-catalysed cyclisations
- 1
Sundberg RJ. Comp. Heterocycl. Chem. (II) Vol. 2:Katritzky AR.Rees CW.Scriven EFV. Elsevier Science; Oxford: 1996. p.119-206 - 2
Gabriele B.Salerno G.Fazio A. J. Org. Chem. 2003, 68: 7853 - 3
Knight DW.Redfern AL.Gilmore J. J. Chem. Soc., Perkin Trans. 1 2002, 622 -
4a
Li JJ.Gribble W. Palladium in Heterocyclic Chemistry, Tetrahedron Organic Chemistry Series Vol. 20: Pergamon Press; Oxford: 2000. -
4b
Wang JJ.Scott AI. Tetrahedron Lett. 1995, 36: 7043 -
4c
Wang JJ.Scott AI. Tetrahedron Lett. 1996, 37: 3247 - 5
Gridley JJ.Coogan MP.Malik KMA.Sharland CM.Singkhonrat J.Williams SM. Chem. Commun. 2003, 2550 - 6
Knight DW.Sharland CM. Synlett 2003, in press -
7a
Glaser C. Ber. Dtsch. Chem. Ges. 1869, 2: 422 -
7b
Kabalka GW.Wang L.Pagni RM. Synlett 2001, 108 -
7c
Eglington G.Galbraith AR. Chem. Ind. (London) 1956, 737 -
7d
Eglington G.McCrae W. Adv. Org. Chem. 1963, 4: 225 -
8a
Clifford AA.Waters WA. J. Chem. Soc. 1963, 3056 -
8b For a recent use of copper salts in a somewhat related cyclisation involving alkynyl imines, see:
Kel’in AV.Sromek AW.Gevorgyan V. J. Am. Chem. Soc. 2001, 123: 2074 - 9
El-Taeb GMM.Evans AB.Knight DW.Jones S. Tetrahedron Lett. 2001, 42: 5945 - 10
Overhand MN.Hecht SM. J. Org. Chem. 1994, 59: 4721 - 12 For a review of electrophile-driven 5-endo cyclisation methods, see:
Knight DW. Prog. Heterocycl. Chem. 2002, 14: 19
References
All products reported herein have been fully characterized by the usual spectroscopic and analytical data and, where possible, by comparisons with known compounds. [3] [6]