Stereochemistry of cyclic ether formation. Part I. Stereoselective intramolecular cyclisation of aliphatic disecondary 1,4-diols and their sulphonate esters to tetrahydrofurans
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2460-2464
- https://doi.org/10.1039/p19720002460
Abstract
Several methods of eliminative cyclisations of diastereoisomeric disecondary 1,4-diols and their 1,4-disulphonate esters, leading to the formation of tetrahydrofurans, have been studied, and it was found that they all proceed stereoselectively by SN2-type mechanisms, with inversion of configuration at one (1,4-diols) or both (1,4-disul-phonates) chiral centres, so that meso(i.e. erythro) 1,4-diols and ±(i.e. threo) 1,4-dimesylates afford only trans-2,5-dialkyl-tetrahydrofurans, while the respective diastereoisomeric substrates are converted exclusively into cis-2,5-dialkyltetrahydrofurans.Keywords
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