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

Journal of Organic Chemistry, ISSN: 1520-6904, Vol: 80, Issue: 13, Page: 6936-6940
2015
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  • 18
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Metrics Details

  • Citations
    7
    • Citation Indexes
      7
  • Captures
    18

Article Description

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.

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