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Synlett 1997; 1997(12): 1423-1425
DOI: 10.1055/s-1997-1054
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Synthesis of 2,5-Disubstituted 3-(Phenylsulfonyl)pyrrolidines via 5-Endo-Trig Cyclisation Reactions

Donald Craig1 , Philip S. Jones2 , Gareth J. Rowlands3
  • 1Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, U.K., fax: +44 171-594 5804; e-mail: dcraig@ic.ac.uk
  • 2Roche Discovery Welwyn, Broadwater Road, Welwyn Garden City, Hertfordshire AL7 3AY, U.K.
  • 3Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, U.K.
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Publication Date:
31 December 2000 (online)

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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.

aziridine - sulfone - pyrrolidine - cyclisation - stereoselective