Chiral base-mediated benzylic functionalisation of tricarbonylchromium(0) complexes of benzylamine derivatives

Susan E Gibson; Mark H Smith

doi:10.1039/b211222c

Chiral base-mediated benzylic functionalisation of tricarbonylchromium(0) complexes of benzylamine derivatives

Org Biomol Chem. 2003 Feb 21;1(4):676-83. doi: 10.1039/b211222c.

Authors

Susan E Gibson¹, Mark H Smith

Affiliation

¹ Department of Chemistry, King's College London, Strand, London, UK WC2R 2LS.

PMID: 12929454
DOI: 10.1039/b211222c

Abstract

The novel complex (eta 6-benzylamine)tricarbonylchromium(0) 11 was prepared in up to 66% yield by direct complexation with Cr(CO)6 in refluxing 1,4-dioxane. Imine derivatives of this complex were readily deprotonated at the benzylic position by diamide 5, and the resultant anions reacted regioselectively with electrophiles (Me3SiCl or MeI) to give fairly good yields of products substituted at the benzylic carbon. Products of up to 87% e.e. were obtained in these reactions, with the highest enantioselectivity being derived from the tert-butyl-substituted imine complex 25.