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Synlett 1998; 1998(10): 1126-1128
DOI: 10.1055/s-1998-1859
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Palladium-Catalysed Cyclisation of Enantiopure Allenic Lactams Prepared from a Pyroglutamic Acid Derived Organozinc Reagent

Willem F. J. Karstens* , Marianne Stol, Floris P. J. T. Rutjes, Henk Hiemstra
  • *Laboratory of Organic Chemistry, Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands; Fax + 31 20 525 5670; E-mail: henkh@org.chem.uva.nl
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Publication Date:
31 December 2000 (online)

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A route for the synthesis of enantiopure allene-substituted lactams has been developed. The key-step involves the copper(I) mediated SN2′ substitution of propargylic tosylates by a (S)-pyroglutamic acid derived organozinc reagent. Pd-catalysed reaction of these allenes with iodobenzene afforded enantiopure bicyclic enamides. Furthermore the unexpected formation of an interesting diene is reported.

organozinc reagents - palladium - catalysis - allenes - enamides - (S)-pyroglutamic acid