dc.contributor.author | Lepage, Romain J | |
dc.contributor.author | Coster, Mark J | |
dc.date.accessioned | 2019-05-29T12:40:36Z | |
dc.date.available | 2019-05-29T12:40:36Z | |
dc.date.issued | 2018 | |
dc.identifier.issn | 0040-4020 | |
dc.identifier.doi | 10.1016/j.tet.2018.01.043 | |
dc.identifier.uri | http://hdl.handle.net/10072/381606 | |
dc.description.abstract | The stereoselective synthesis of 5,5-spiroacetals by Rh(II)-catalysed double C–H insertion of methylene acetals bearing two diazo ester substituents is described. The diastereoselectivity of this bidirectional approach can be tuned through appropriate choice of catalyst, and chiral catalysts lead to products with up to 89% ee. The diastereoselectivity of the first cyclisation suggests that the second cyclisation proceeds via a non-concerted pathway. | |
dc.description.peerreviewed | Yes | |
dc.language | English | |
dc.language.iso | eng | |
dc.publisher | Elsevier | |
dc.publisher.place | United Kingdom | |
dc.relation.ispartofpagefrom | 1313 | |
dc.relation.ispartofpageto | 1321 | |
dc.relation.ispartofissue | 12 | |
dc.relation.ispartofjournal | Tetrahedron | |
dc.relation.ispartofvolume | 74 | |
dc.subject.fieldofresearch | Medicinal and biomolecular chemistry | |
dc.subject.fieldofresearch | Organic chemistry | |
dc.subject.fieldofresearch | Organic chemistry not elsewhere classified | |
dc.subject.fieldofresearchcode | 3404 | |
dc.subject.fieldofresearchcode | 3405 | |
dc.subject.fieldofresearchcode | 340599 | |
dc.subject.keywords | Spiroacetal | |
dc.subject.keywords | Bidirectional | |
dc.subject.keywords | C–H insertion | |
dc.subject.keywords | Stereoselectivity | |
dc.subject.keywords | Rh(II)-catalysis | |
dc.title | Stereoselective bidirectional synthesis of spiroacetals via Rh(II)-catalysed double C-H insertion | |
dc.type | Journal article | |
dc.type.description | C1 - Articles | |
dc.type.code | C - Journal Articles | |
dcterms.license | http://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.description.version | Accepted Manuscript (AM) | |
gro.faculty | Griffith Sciences, School of Environment and Science | |
gro.rights.copyright | © 2018 Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International Licence which permits unrestricted, non-commercial use, distribution and reproduction in any medium, providing that the work is properly cited. | |
gro.hasfulltext | Full Text | |
gro.griffith.author | Coster, Mark J. | |
gro.griffith.author | Lepage, Romain | |