biostudies-literatureUnknown15(3)Hou JInspired by the high affinity of copper with DNA and RNA, a uracil-copper catalytic system was developed to promote ring-opening allylation of cyclopropanols with allylic alcohols under water-tolerant conditions. A new C-OH bond-breaking model can well resolve the trade-off between the need for acidic activators for C(allyl)-OH bond cleavage and the demand for strong basic conditions for generating homoenolates. Therefore, Morita-Baylis-Hillman alcohols, rather than their pre-activated versions, could be incorporated directly into dehydrative cross-coupling with cyclopropanols delivering water as the only by-product. A variety of functionalized δ,ε-unsaturated ketones were obtained in good-to-high yield with high E-selectivity.Chemical science1143-1149https://www.ebi.ac.uk/biostudies/studies/S-EPMC10793597biostudies-literatureUracil-Cu(i) catalyst: allylation of cyclopropanols with Morita-Baylis-Hillman alcohols under water-tolerant conditions.PMC10793597Li XHou JYan KZhang LLoh TPXie PfalseUracil-Cu(i) catalyst: allylation of cyclopropanols with Morita-Baylis-Hillman alcohols under water-tolerant conditions.Inspired by the high affinity of copper with DNA and RNA, a uracil-copper catalytic system was developed to promote ring-opening allylation of cyclopropanols with allylic alcohols under water-tolerant conditions. A new C-OH bond-breaking model can well resolve the trade-off between the need for acidic activators for C(allyl)-OH bond cleavage and the demand for strong basic conditions for generating homoenolates. Therefore, Morita-Baylis-Hillman alcohols, rather than their pre-activated versions, could be incorporated directly into dehydrative cross-coupling with cyclopropanols delivering water as the only by-product. A variety of functionalized δ,ε-unsaturated ketones were obtained in good-to-high yield with high E-selectivity.2024-01-01T00:00:00Z2024 Jan2025-04-26T07:33:33.913Z2025-04-06T12:19:25.696ZS-EPMC107935973823970010.1039/d3sc04890j