New transformations from a 3-silyloxy 2-aza-1, 3-diene: consecutive Zr-mediated retro-brook rearrangement and reactions with electrophiles
V Gandon, P Bertus, J Szymoniak
Index: Gandon, Vincent; Bertus, Philippe; Szymoniak, Jan Tetrahedron, 2000 , vol. 56, # 26 p. 4467 - 4472
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Citation Number: 9
Abstract
A one-pot procedure for the transformation of the title compound to α-functionalized (silylated) and α, β-unsaturated secondary amides was described. The following steps were involved: a Zr-mediated retro-Brook rearrangement, selective deprotonation with n-BuLi on the organometallic intermediate, and trapping with electrophiles including alkyl and acyl halides and aldehydes. The electrophilic addition step occurred at a stabilized α-silyl ...
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