Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 18, Pages 3251-3259Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900710
Keywords
N-alkoxycarbonylamino sulfones; allylation; bismuth; ring-closing metathesis; Sakurai reaction; silanes
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Fonds Quebecois de la Recherche sur la Nature et les Technologies (FQRNT, Quebec, Canada)
- Canada Foundation for Innovation
- Universite Laval
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Bismuth triflate was found to be an efficient catalyst in the Sakurai reaction of allyltrimethylsilanes with N-alkoxycarbonylamino sulfones. The reaction proceeded smoothly with a low catalyst loading of Bi(OTf)(3)center dot 4H(2)O (2-5 mol%) to afford the corresponding protected homoallylic amines in very good yields (up to 96%). A sequential allylation reaction followed by ring-closing metathesis delivers 6-8 membered 3-Cbz-protected cycloalkenylamines.
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