Synlett 2001; 2001(1): 0141-0143
DOI: 10.1055/s-2001-9718
© 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.

Diastereoselective Synthesis of Enantiopure C 2-Symmetric Dihaloferrocenes

Andrew J. Locke* , Tom E. Pickett, Christopher J. Richards
  • *Department of Chemistry, Cardiff University, P O Box 912, Cardiff, CF103/TB, U. K.; Fax +44(0)29-20 87 40 30; E-mail:
Further Information

Publication History

Publication Date:
31 December 2001 (online)

1,1′-bis[(S)-4-isopropyloxazolin-2-yl]ferrocene was dilithiated with sec-BuLi/TMEDA in Et2O to give a (p R:p R):(p R:p S) selectivity of 10:1. Following addition of C2Cl6 or C2Br2Cl4 the resulting dichloro and dibromo derivatives were subjected to oxazoline ring opening and further manipulation to provide enantiopure (p S,p S)-1,1′-dicarbomethoxy-2,2′-dihaloferrocenes, (p S,p S)-1,1′-di(hydroxymethyl)-2,2′-dihaloferrocenes and (p S,p S)-1,1′-dicarbaldehyde-2,2′-dihaloferrocenes.