Facile Formation of β-Hydroxyboronate Esters by a Cu-Catalyzed Diboration/Matteson Homologation Sequence

نویسندگان

  • Cameron M. Moore
  • Casey R. Medina
  • Peter C. Cannamela
  • Melissa L. McIntosh
  • Carl J. Ferber
  • Andrew J. Roering
  • Timothy B. Clark
چکیده

The copper-catalyzed diboration of aldehydes was used in conjunction with the Matteson homologation, providing the efficient synthesis of β-hydroxyboronate esters. The oxygen-bound boronate ester was found to play a key role in mediating the homologation reaction, which was compared to the α-hydroxyboronate ester (isolated hydrolysis product). The synthetic utility of the diboration/homologation sequence was demonstrated through the oxidation of one product to provide a 1,2-diol.

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عنوان ژورنال:

دوره 16  شماره 

صفحات  -

تاریخ انتشار 2014