Synthesis and atropisomeric stability of 2,2′-bis(ferrocenylhydroxymethyl)-1,1′-biphenyl

Diol 1 was obtained in three diastereoisomeric forms, depending on the different combinations of central and axial chirality, with sufficient atropisomeric stability to allow their detection and separation. Nickel(0)-mediated homocoupling of (2-bromobenzoyl)ferrocene gave in high yield diketone 4 po...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2005-03, Vol.16 (5), p.965-970
Main Authors: Patti, Angela, Pedotti, Sonia
Format: Article
Language:English
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Summary:Diol 1 was obtained in three diastereoisomeric forms, depending on the different combinations of central and axial chirality, with sufficient atropisomeric stability to allow their detection and separation. Nickel(0)-mediated homocoupling of (2-bromobenzoyl)ferrocene gave in high yield diketone 4 possessing a biphenyl unit. Its chemical reduction afforded the title compound in three diastereomeric forms 1a–c with sufficient atropisomeric stability to allow their detection and purification. By rotation around the biphenyl bond, enantiomers of 1a suffered racemization whereas diol 1c isomerized to b, which resulted in being atropisomerically stable since the reverse process from 1b to c did not occur. Activation parameters for both these atropisomerizations were also determined. The observed conformational stability can be explained by both hydrogen bonding and steric interactions.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2004.12.025