Tethering for Selective Synthesis of 2,2′-Biphenols : the Acetal Method
Masters, Kye-Simeon, Bihlmeier, Angela, Klopper, Wim, & Bräse, Stefan (2013) Tethering for Selective Synthesis of 2,2′-Biphenols : the Acetal Method. Chemistry : A European Journal, 19(52), pp. 17827-17835.
2,2'-Biphenols are a large and diverse group of compounds with exceptional properties both as ligands and bioactive agents. Traditional methods for their synthesis by oxidative dimerisation are often problematic and lead to mixtures of ortho- and para-connected regioisomers. To compound these issues, an intermolecular dimerisation strategy is often inappropriate for the synthesis of heterodimers. The ‘acetal method’ provides a solution for these problems: stepwise tethering of two monomeric phenols enables heterodimer synthesis, enforces ortho regioselectivity and allows relatively facile and selective intramolecular reactions to take place. The resulting dibenzo[1,3]dioxepines have been analysed by quantum chemical calculations to obtain information about the activation barrier for ring flip between the enantiomers. Hydrolytic removal of the dioxepine acetal unit revealed the 2,2′-biphenol target.
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|Item Type:||Journal Article|
|Subjects:||Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > ORGANIC CHEMISTRY (030500)
Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > ORGANIC CHEMISTRY (030500) > Natural Products Chemistry (030502)
Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > ORGANIC CHEMISTRY (030500) > Organic Chemical Synthesis (030503)
|Divisions:||Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
|Copyright Owner:||Copyright 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim|
|Deposited On:||03 Apr 2014 01:55|
|Last Modified:||03 Apr 2014 21:33|
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