Organic Chemistry Portal

Abstracts

Search:

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 (free Supporting Information)


Abstract

CsF with 1.1 equiv of H2O effects highly efficient protodeboronation on tertiary diarylalkyl boronic esters with essentially complete retention of configuration, whereas TBAFˇ3H2O 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



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.


Key Words

Benzylation, Benzylboronates, Protodeboronation


ID: J48-Y2010-3330