Journal
HETEROCYCLES
Volume 99, Issue 1, Pages 248-266Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-18-S(F)18
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Funding
- Ministerio de Economia y Competitividad (MINECO) [CTQ2014-53695-P, CTQ2014-51912-REDC, CTQ2016-81797-REDC, CTQ2017-85093-P]
- FEDER
- Generalitat Valenciana [PROMETE011/2014/017]
- University of Alicante
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The reaction of N-tert-butanesulfinyl imines 1 with 1,3-dibromopropene (2), in the presence of indium metal, in saturated aqueous solution of sodium bromide, produced bromohomoallylamine derivatives 3 with total facial diastereoselectivity for the imine addition, and moderate yields. These compounds were easily transformed into the corresponding vinyl aziridines 5 upon deprotonation with KHMDS in THF, the intramolecular cyclization taking place in a stereospecific manner in moderate to high yields.
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