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

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

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 pr...

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Veröffentlicht in:Journal of organic chemistry 2015-07, Vol.80 (13), p.6936-6940
Hauptverfasser: Drouillat, B, Wright, K, Quinodoz, P, Marrot, J, Couty, F
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01230