Synthesis 1996; 1996(6): 707-710
DOI: 10.1055/s-1996-4278
paper
© 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.

Phosphoryl Functionalized Bishomoallyl Alcohols by Ring Opening of Epoxides with Lithiated Allyldiphenylphosphane Oxide

Jens-Kerim Ergüden, Ernst Schaumann*
  • *Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstr. 6, D-38678 Clausthal-Zellerfeld, Germany, Fax +49(5323)722858; e-mail: schaumann@ioc.tu-clausthal.de
Further Information

Publication History

Publication Date:
31 December 2000 (online)

Epoxides are attacked by the lithiated anion of allyldiphenylphosphane oxide in 1,2-dimethoxyethane as solvent in a boron trifluoride-diethyl ether complex promoted ring opening reaction to afford a mixture of regioisomeric bishomoallyl alcohols - and γ-attack of the nucleophile) in good overall yields. When toluene is used as reaction medium a pronounced preference for γ-attack of the anion is observed.