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Carbenium ion trapping using sulfonamides: an acid-catalysed synthesis of pyrrolidines by intramolecular hydroamination

Griffiths-Jones, Charlotte M. and Knight, David William 2010. Carbenium ion trapping using sulfonamides: an acid-catalysed synthesis of pyrrolidines by intramolecular hydroamination. Tetrahedron 66 (23) , pp. 4150-4166. 10.1016/j.tet.2010.03.107

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Abstract

Cyclisations of homoallylic sulfonamides proceed smoothly via carbeniumion 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 carbeniumions. 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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: Cyclisation; Hydroamination; Sulfonamides; Triflic acid; Pyrrolidines
Publisher: Elsevier
ISSN: 0040-4020
Last Modified: 04 Jun 2017 03:28
URI: http://orca.cf.ac.uk/id/eprint/21726

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