Affordable Access

Publisher Website

Selective synthesis of ferrocenes

Authors
Journal
Journal of Organometallic Chemistry
0022-328X
Publisher
Elsevier
Publication Date
Volume
567
Identifiers
DOI: 10.1016/s0022-328x(98)00682-2
Keywords
  • Iron
  • Chiral Ferrocenes
  • One Pot Synthesis
  • Chiral Ferrocenophanes

Abstract

Abstract We have developed a new one pot procedure for the selective functionalization of the 1′ position in ferrocenecarbaldehyde, with fair yields (up to 70%) and good regioselectivity (>90/10). Our method uses lithium N-methylpiperazide as a temporary protecting group of the aldehyde function and directing group for lithiation on the unsubstituted cyclopentadienyl ring of ferrocene. The extension of this new method with enantiomerically pure 2-substituted ferrocenecarbaldehydes provides an easy access to various enantiomerically pure 1,2,1′-trisubstituted ferrocenes with three different groups. Finally, when applying our method for the lithiation of 1,1′-ferrocenedicarbaldehyde with a chiral amine, we found a one pot synthesis of 1,2,1′,2′-tetrasubstituted C 2-symmetrical ferrocenes with very high enantiomeric excesses (>99%). Furthermore, changing the experimental conditions allows us to obtain 1,2,1′-trisubstituted ferrocenes with a very good enantioselectivity (up to 96%). The first chiral enantiomerically pure 2-substituted 1,1′-( β- oxa-trimethylene)ferrocenes and the first chiral enantiomerically pure C 2-symmetrical-disubstituted 1,1′-( β- oxa-trimethylene)ferrocene were also synthesized.

There are no comments yet on this publication. Be the first to share your thoughts.

Statistics

Seen <100 times
0 Comments

More articles like this

Bridged ferrocenes:VII. Synthesis of di- and tri-b...

on Journal of Organometallic Chem... Jan 01, 1981

The synthesis and properties of bis-1,1'-(porphyri...

on Organic & Biomolecular Chemist... Jul 21, 2005

Synthesis and properties of azole-substituted ferr...

on Journal of Organometallic Chem... Jan 01, 2006
More articles like this..