Tetrahedron

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

L Ma, D Zhao, L Chen, X Wang, YL Chen, J Shen

Index: Ma, Lu; Zhao, Dongmei; Chen, Lin; Wang, Xin; Chen, Yue-Lei; Shen, Jingkang Tetrahedron, 2012 , vol. 68, # 42 p. 8704 - 8711

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Citation Number: 4

Abstract

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 ...