Protodeboronation of Tertiary Boronic Esters: Asymmetric Synthesis of Tertiary Alkyl Stereogenic Centers

Stefan Nave, Ravindra P. Sonawane, Tim G. Elford and Varinder K. Aggarwal*

*School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K., Email: v.aggarwalbristol.ac.uk

S. Nave, R. P. Sonawane, T. G. Elford, V. K. Aggarwal, J. Am. Chem. Soc., 2010, 132, 17096-17098.

DOI: 10.1021/ja1084207

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Abstract

CsF with 1.1 equiv of H₂O effects highly efficient protodeboronation on tertiary diarylalkyl boronic esters with essentially complete retention of configuration, whereas TBAF·3H₂O can be used for tertiary aryldialkyl boronic esters. Furthermore, substituting D₂O for H₂O provides ready access to deuterium-labeled enantioenriched tertiary alkanes. A short synthesis of the sesquiterpene (S)-turmerone is described.

see article for more examples

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Synthesis of Enantioenriched Tertiary Boronic Esters by the Lithiation/Borylation of Secondary Alkyl Benzoates

A. P. Pulis, D. J. Blair, E. Torres, V. K. Aggarwal, J. Am. Chem. Soc., 2013, 135, 16054-16057.

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Key Words

Benzylation, Benzylboronates, Protodeboronation

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ID: J48-Y2010-3330