Stereoselectivity in electrophile-mediated cyclisations. Ag I -Catalysed synthesis of disubstituted pyrrolidines; crystal structure of cis-5-phenyl-N-tosylpyrrolidin-2-ylmethyl 4-bromobenzoate
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 9,p. 2193-2198
- https://doi.org/10.1039/p19910002193
Abstract
A series of phenyl-substituted allenic sulphonamides 5, 6 and 7 have been prepared and shown to ndergo AgI-catalysed cyclisation to give the corresponding 2,5-, 2,4- and 2,3-disubstituted N-sulphonylpyrrolidines 8, 9, and 10 respectively. The interactions between substituents in the ringforming step play a key role in controlling the cis/trans selectivity observed in cyclisations involving 5(cis-selective) and 7(trans-selective). AgI-Catalysed cyclisation of 6 to give the 2,4-disubstituted pyrrolidine 9 was, however, nonselective.Keywords
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