Download PDF
Synlett 1996; 1996(1): 18-20
DOI: 10.1055/s-1996-5313
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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