Journal
TETRAHEDRON
Volume 66, Issue 23, Pages 4150-4166Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.03.107
Keywords
Cyclisation; Hydroamination; Sulfonamides; Triflic acid; Pyrrolidines
Categories
Funding
- University of Melbourne
- EPSRC through DTA
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Cyclisations of homoallylic sulfonamides proceed smoothly via carbenium ion generation using trifluoromethanesulfonic (triflic) acid, the ease of cyclisation being directly related to the ion stability to give good to excellent yields of the corresponding pyrrolidines. Both toluene- and nitrophenyl-sulfonyl groups are suitable for all substrates tested whereas the corresponding carbamates are only useful in cases of tertiary and highly stabilised carbenium ions. Polyene-derived sulfonamides can also be cyclised to the corresponding polycyclic systems in remarkably high yields, in reactions reminiscent of related cascades encountered in terpene biosynthesis. (C) 2010 Elsevier Ltd. All rights reserved.
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