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Synlett 1996; 1996(1): 18-20
DOI: 10.1055/s-1996-5313
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Iron-Mediated Allylic Substitutions with Complete Chirality Transfer. Synthesis of Functionalized γ-Substituted Alkenylsulfones of High Enantiomeric Purity

Dieter Enders* , Stefan von Berg, Bernd Jandeleit
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany
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Publication Date:
31 December 2000 (online)

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The nucleophilic addition of various functionalized copper-zinc-reagents 4 to the highly enantiomerically enriched 1-phenylsulfonyl substituted planar chiral tetracarbonyl (η 3-allyl)iron(1+)tetrafluoroborate 3 provides after oxidative removal of the tetracarbonyliron group highly functionalized γ-substituted alkenylsulfones 5 of high enantiomeric purity (ee > 96-99 %). The reaction is highly regio- and stereoselective and proceeds in moderate to good yields (33-83 %) retaining the double bond geometry and with virtually complete chirality transfer (C-O to C-C) with respect to the starting material 1.

allylic substitution - tetracarbonyl(η 3-allyl)iron(1+) complexes - chirality transfer - zinc-copper reagents - alkenylsulfones

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