期刊
TETRAHEDRON
卷 66, 期 23, 页码 4150-4166出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.03.107
关键词
Cyclisation; Hydroamination; Sulfonamides; Triflic acid; Pyrrolidines
资金
- University of Melbourne
- EPSRC through DTA
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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