Diastereofacial selectivity in Diels–Alder reactions of buta-1,3-dienes having stereogenic allylic heteroatom substituents at the C-2 position
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 13,p. 953-955
- https://doi.org/10.1039/c39920000953
Abstract
Diels–Alder reactions of ten 2-substituted buta-1,3-dienes 1a–j with N-phenylmaleimide were examined under various conditions, demonstrating that an allylic heteroatom substiuent at the C-2 position exerts significant directing effect on diastereofacial selection and also that the diastereofacial selectivity can be enhanced by use of 5 mol dm–3 LiClO4–Et2O as a reaction medium.Keywords
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