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Synlett 1991; 1991(6): 397-400
DOI: 10.1055/s-1991-20740
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Synthesis of Enantiomerically Enriched Allenes via Chiral, Configurationally Stable 1-Lithio-2-alkynyl Carbamates

S. Dreller* , M. Dyrbusch, D. Hoppe
  • *Institut für Organische Chemie der Universität Kiel, Olshausenstr. 40, D-2300 Kiel 1, Germany
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Publication Date:
07 March 2002 (online)

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Enantiomerically enriched, configurationally stable propargylic anions 5 are produced by deprotonation of optically active secondary 2-alkynyl N,N-diisopropylcarbamates 4. The lithium intermediates 5 add aldehydes with a high degree of chirality transfer in the formation of the allenyl carbinols 7 and 8 [(4-hydroxy-1,2-alkadienyl) N,N-diisopropylcarbamates]. A method for trapping short-lived chiral carbanions is introduced, which is based on the deprotonation of the optically active precursor 4 with sec-butyllithium in the presence of pivalaldehyde.

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