Synlett 2005(14): 2159-2162  
DOI: 10.1055/s-2005-872240
LETTER
© Georg Thieme Verlag Stuttgart · New York

Exploiting Planar Chirality for the Generation of α-Ferrocenyl Stereogenic Centres

Caroline J. Taylor, Francesc X. Roca, Christopher J. Richards*
Department of Chemistry, Queen Mary, University of London, Mile End Road, London, E1 4NS, UK
Fax: +44(20)78827794; e-Mail: c.j.richards@qmul.ac.uk;
Further Information

Publication History

Received 7 April 2005
Publication Date:
22 July 2005 (eFirst)

Abstract

Addition of Grignard reagents R1MgBr (R1 = Me, Et, i-Pr, t-Bu, Ph) to 2-bromo- and 2-trimethylsilylferrocenecarboxaldehyde proceeded, in most cases, with high diastereoselectivity to generate α-ferrocenyl alcohols of S*,p S* configuration. Following conversion into their corresponding acetates, reaction with dimethylamine provided α-ferrocenyl amines with retention of configuration (R1 = Me, Et, Ph).