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Synlett 2004(1): 119-121  
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

David W. Knight*, Christopher M. Sharland
Cardiff School of Chemistry, Cardiff University, P.O. Box 912, Cardiff, CF10 3TB, UK
e-Mail: knightdw@cardiff.ac.uk;
Further Information

Publication History

Received 27 October 2003
Publication Date:
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

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11

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]