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

Cameron M. Moore | Zendy; Casey R. Medina | Zendy; Peter C. Cannamela | Zendy; Melissa L. McIntosh | Zendy; Carl J. Ferber | Zendy; A.J. Roering | Zendy; Timothy Clark | Zendy

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

Author(s) -

Cameron M. Moore,

Casey R. Medina,

Peter C. Cannamela,

Melissa L. McIntosh,

Carl J. Ferber,

A.J. Roering,

Timothy Clark

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502767m

Subject(s) - chemistry , sequence (biology) , catalysis , hydrolysis , diol , oxygen , copper , organic chemistry , combinatorial chemistry , biochemistry

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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