Synthesis of 25-Disubstituted 3-(Phenylsulfonyl)pyrrolidines via 5-i Endo- Trig Cyclisation Reactions

Craig, Donald, Jones, Philip S and Rowlands, Gareth J (1997) Synthesis of 25-Disubstituted 3-(Phenylsulfonyl)pyrrolidines via 5-i Endo- Trig Cyclisation Reactions. Synlett, 12. 1423 - 1426. ISSN 0936-5214

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Abstract

Reaction of lithiated (phenylsulfonyl)methane with enantiomerically pure N-diphenylphosphinylaziridines gives adducts 4, which may be acylated at the sulfone α-position by further lithiation and reaction with non-enolisable acid chlorides, giving ketones 5. Reduction followed by acetylation gives substrates 6, which undergo elimination and 5-endo-trig cyclisation to give 2,5-disubstituted 3-(phenylsulfonyl)pyrrolidines 7 in high yields and with excellent stereoselectivities. Some further reactions of the pyrrolidines are described.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: EPrints Services
Date Deposited: 06 Feb 2012 21:16
Last Modified: 17 Jul 2013 15:14
URI: http://sro.sussex.ac.uk/id/eprint/30560
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