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

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• 作者：Lu Ma ; Dongmei Zhao ; Lin Chen ; Xin Wang ; Yue-Lei Chen ; Jingkang Shen
• 关键词：Nucleophilic addition ; Aldehydes ; N ; N-Diisopropylcarbamoyl ; Regioselective protection ; 1 ; 2-Diols
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：21 October, 2012
• 年：2012
• 卷：68
• 期：42
• 页码：8704-8711
• 全文大小：866 K

文摘

1-(N,N-Diisopropylcarbamoyloxy)-1-tosyl-methane (CbOCH₂Ts, Cb=N,N-diisopropylcarbamoyl) was readily prepared from p-TolSH, 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.