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Synlett 2001; 2001(1): 0141-0143
DOI: 10.1055/s-2001-9718
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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: RichardsCJ@cardiff.ac.uk
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Publikationsdatum:
31. Dezember 2001 (online)

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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.

ferrocenes - diastereoselectivity - halogens - metallations - oxazolines

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