(N,N-Diisopropylcarbamoyloxy)-methyl p-tolyl sulfone: preparation and application for the syntheses of 1,2-diols

1-(N,N-Diisopropylcarbamoyloxy)-1-tosyl-methane (CbOCH2Ts, Cb=N,N-diisopropylcarbamoyl) was readily prepared from p-ToISH, paraformaldehyde and CbCl. With the dual activation of CbO- and Ts-substitutions, deprotonation of CbOCH2Ts could be effected not only by n-BuLi, but also by Grignard reagents. Upon deprotonation, the title compound adds to various carbonyl structures. By choosing proper organometallic reagents for consecutive steps, the addition intermediate undergoes in situ conversions to efficiently yield regioselectively O-Cb protected and unprotected 1,2-diols. (C) 2012 Elsevier Ltd. All rights reserved.