dc.contributor.author | Sahari, Aleksi | |
dc.contributor.author | Do, Cuong Dat | |
dc.contributor.author | Mannisto, Jere K. | |
dc.contributor.author | Antico, Emanuele | |
dc.contributor.author | Amaratunga, Angelo | |
dc.contributor.author | Hopmann, Kathrin Helen | |
dc.contributor.author | Repo, Timo | |
dc.date.accessioned | 2022-03-30T07:08:02Z | |
dc.date.available | 2022-03-30T07:08:02Z | |
dc.date.issued | 2022-02-14 | |
dc.description.abstract | We report a Ti(OiPr)4-mediated multicomponent reaction, which
produces 3,4-substituted cis-d-lactones from alkyl magnesium
chloride, benzaldehyde and CO<sub>2</sub>. The key intermediate, titanacyclopropane, is formed in situ from Ti(OiPr)4 and a Grignard reagent,
which enables 1,2-dinucleophilic reactivity that is used to insert
carbon dioxide and an aldehyde. An alternative reaction route is
also described where a primary alkene is used to create the
titanacyclopropane. A computational analysis of the elementary
steps shows that the carbon dioxide and the aldehyde insertion
proceeds through an inner-sphere mechanism. A variety of cisbutyrolactones can be synthesized with up to 7 : 1 diastereoselectivity and 77% yield. | en_US |
dc.identifier.citation | Sahari A, Do CD, Mannisto JK, Antico, Amaratunga, Hopmann KH, Repo T. Titanium isopropoxide-mediated cis-selective synthesis of 3,4-substituted butyrolactones from CO2. Chemical Communications. 2022;58:3027-3030 | en_US |
dc.identifier.cristinID | FRIDAID 2006889 | |
dc.identifier.doi | https://doi.org/10.1039/D2CC00446A | |
dc.identifier.issn | 1359-7345 | |
dc.identifier.issn | 1364-548X | |
dc.identifier.uri | https://hdl.handle.net/10037/24638 | |
dc.language.iso | eng | en_US |
dc.publisher | Royal Society of Chemistry | en_US |
dc.relation.journal | Chemical Communications | |
dc.relation.uri | https://pubs.rsc.org/en/content/articlelanding/2022/CC/D2CC00446A#fn1 | |
dc.rights.accessRights | openAccess | en_US |
dc.rights.holder | Copyright 2022 The Author(s) | en_US |
dc.title | Titanium isopropoxide-mediated cis-selective synthesis of 3,4-substituted butyrolactones from CO2 | en_US |
dc.type.version | publishedVersion | en_US |
dc.type | Journal article | en_US |
dc.type | Tidsskriftartikkel | en_US |
dc.type | Peer reviewed | en_US |