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

journal contribution
posted on 2023-06-08, 09:31 authored by Donald Craig, Philip S Jones, Gareth J Rowlands
Reaction of lithiated (phenylsulfonyl)methane with enantiomerically pure N-diphenylphosphinylaziridines gives adducts 4, which may be acylated at the sulfone a-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.

History

Publication status

  • Published

Journal

Synlett

ISSN

0936-5214

Publisher

Thieme ejournals

Volume

12

Page range

1423 - 1426

ISBN

0936-5214

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-02-06

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