Synthesis and properties of chiral ferrocenylalcohols and diols (Contributo in volume (capitolo o saggio))

  • Synthesis and properties of chiral ferrocenylalcohols and diols (Contributo in volume (capitolo o saggio)) (literal)
  • 2010-01-01T00:00:00+01:00 (literal)
Alternative label
  • Angela Patti; Sonia Pedotti (2010)
    Synthesis and properties of chiral ferrocenylalcohols and diols
    Nova Science Publishers, New York (Stati Uniti d'America) in Organometallic compounds: preparation, structure and properties, 2010
  • Angela Patti; Sonia Pedotti (literal)
Pagina inizio
  • 255 (literal)
Pagina fine
  • 291 (literal)
  • New York (literal)
  • (literal)
  • Organometallic compounds: preparation, structure and properties (literal)
  • 37 (literal)
  • Istituto di Chimica Biomolecolare del CNR, via Paolo Gaifami 18, I-95126 Catania, Italy (literal)
  • Synthesis and properties of chiral ferrocenylalcohols and diols (literal)
  • Organometallic Compounds: Preparation, structure and properties (literal)
  • 978-1-60741-917-4 (literal)
  • Chin, H. F. (literal)
  • Chiral ferrocenyl derivatives find applications in different fields of chemistry, the most important being their use as ligands in asymmetric catalysis. The peculiar chemistry of the metallocene system makes possible a modular and selective modification of the structure of ferrocene-based catalysts in order to achieve a fine tuning of their electronic and steric properties and improve the efficiency and stereoselectivity of the asymmetric reaction. Although the major part of ferrocenyl ligands are P,N- or N,N-ligands, their preparation often uses chiral ferrocenylalcohols or diols as starting material and different protocols can be applied on the basis of the structural pattern of the target ferrocene. A classification of chiral ferrocenylalcohols and diols according to their structure and, consequently, their stereochemical properties, is here proposed and the related preparation methods are reviewed with a main focus on the asymmetric reactions rather than the racemate resolution procedures. The asymmetric reduction of achiral ferrocenylketones has gained much interest since the corresponding optically active ?-ferrocenylalcohols experience nucleophilic substitution of the hydroxyl group with complete retention of configuration giving access to a large number of homochiral derivatives. Asymmetric hydrogenation as well as reduction with borane as hydride source have been found effective in the preparation of alpha-ferrocenylalcohols and have been applied to a variety of ferrocenylketones and diketones. Asymmetric Sharpless' dihydroxylation of ferrocenylalkenes has been exploited for the synthesis of some ferrocenyldiols whereas a number of difunctionalised alcohols have been obtained by reaction of ferrocenecarboxaldehydes with chiral reagents. The large group of planar chiral ferrocenylalcohols is mainly characterized by the 1,2-substitution pattern and they are usually prepared in enantiopure form through diastereoselective metalation of some suitable chiral ferrocenes followed by electrophilic quenching of the intermediate ferrocenyl carbanion. A short survey of the properties of ferrocenylalcohols, including their chemical behavior and methods useful for their characterization is also presented, together with the more recently reported application of O,N- or O,O-ferrocene ligands in asymmetric catalysis. (literal)
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