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DOI: 10.1055/s-2007-980341
Investigations of the [2,3]-Sigmatropic Rearrangements of Vinylaziridines and Allylic Amines
Publikationsverlauf
Publikationsdatum:
08. Mai 2007 (online)
Abstract
This account summarizes our studies of [2,3]-sigmatropic rearrangements of vinylaziridines and allylic amines. The scope and limitations of the reactions as well as our present mechanistic understanding are also discussed.
1 Introduction
2 Aza-[2,3]-Wittig Rearrangement of Vinylaziridines
2.1 Early Attempts
2.2 Synthesis of Vinylaziridines
2.3 Rearrangement of Vinylaziridines
2.4 Total Synthesis of Indolizidines (-)-209B and (-)-209D
3 [2,3]-Sigmatropic Rearrangement of Allylic Amines
3.1 Lewis Acid Mediated Rearrangements
3.2 Asymmetric Rearrangements
4 Conclusions
Key words
rearrangements - vinylaziridines - ylides - pericyclic reactions - asymmetric reactions
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References and Notes
Somfai P., unpublished results.
21Ottosson H., Somfai P., unpublished results.
32InCl3 and ZnCl2 gave low yields; other unsuccessful Lewis acids were CuCl, CuCl2, TiCl4, Yb(OTf)3, FeCl3, ZrCl2Cp2, and ScCl3.
40PhMe: 70% yield, er ≥ 98.5:1.5; Et2O: 27% yield,
er ≥ 98.5:1.5; THF: 15% yield, er = 92:8.