Aza-[2,3]-Wittig Sigmatropic Rearrangement of Allylic Tertiary Amines: A Successful Example with High Chirality Transfer

作者:Drouillat B; Wright K; Quinodoz P; Marrot J; Couty F*
来源:Journal of Organic Chemistry, 2015, 80(13): 6936-6940.
DOI:10.1021/acs.joc.5b01230

摘要

We report herein a successful example of an aza-[2,3]-Wittig rearrangement in an allylic tertiary N,N-dibenzyl amine derived from (S)-alaninol or (S)-isoleucinol. This reaction occurs upon metalation at the benzylic position with a mixture of butyllithium/diisopropylamine/potassium t-butoxide and proceeds with a high 1,3 transfer of chirality.

  • 出版日期2015-7-3