Spiro-C(sp3)-atom transfer: Creating rigid 3D structures with Ph2SCN2
| dc.contributor.author | Sun, Qiu | |
| dc.contributor.author | Belting, Jan-Niklas | |
| dc.contributor.author | Hauda, Julian | |
| dc.contributor.author | Tymann, David | |
| dc.contributor.author | Antoni, Patrick W. | |
| dc.contributor.author | Goddard, Richard | |
| dc.contributor.author | Hansmann, Max M. | |
| dc.date.accessioned | 2025-02-21T11:28:32Z | |
| dc.date.available | 2025-02-21T11:28:32Z | |
| dc.date.issued | 2025-02-21 | |
| dc.description.abstract | The introduction of a single C-atom into organic substrates typically results in the formation of flat molecules containing unsaturated C(sp)-centers. Adding a single C(sp3)-atom surrounded by four σ-C–C bonds, which opens up the three-dimensional space, is an unresolved problem in synthetic chemistry. We report the synthesis and application of the diazosulfur ylide Ph2S=C=N2 reagent that combines the reactivity of both sulfur ylides and diazo compounds to create carbon spiro-centers in a general fashion by the sequential or single-step installation of a C(sp3)-atom. New C–C and C–X (where X is O or N) bonds can be created around the C(sp3)-atom, which can ultimately be extended to four C–C σ-bonds in one step without resorting to transition metal catalysis. Ph2SCN2 can also be used to access highly strained frameworks containing (oxa)spiro[2.2]pentanes as well as tricyclic spiro-compounds. | en |
| dc.identifier.uri | http://hdl.handle.net/2003/43485 | |
| dc.identifier.uri | http://dx.doi.org/10.17877/DE290R-25318 | |
| dc.identifier.uri | http:/dx.doi.org/10.1126/science.ads5974 | |
| dc.language.iso | en | |
| dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | |
| dc.subject.ddc | 540 | |
| dc.title | Spiro-C(sp3)-atom transfer: Creating rigid 3D structures with Ph2SCN2 | en |
| dc.type | Text | |
| dc.type.publicationtype | Article | |
| dcterms.accessRights | open access | |
| eldorado.secondarypublication | true | |
| eldorado.secondarypublication.primarycitation | Qiu Sun et al., Spiro-C(sp3)-atom transfer: Creating rigid three-dimensional structures with Ph2SCN2.Science387,885-892(2025).DOI:10.1126/science.ads5974 | |
| eldorado.secondarypublication.primaryidentifier | http:/dx.doi.org/10.1126/science.ads5974 |