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Arylboronic acid-catalyzed racemization of secondary and tertiary alcohols
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dc.contributor.author | Boyce, Gregory | |
dc.contributor.author | Musolino, Stefania F. | |
dc.contributor.author | Yang, Jianing | |
dc.contributor.author | Smith, Andrew D. | |
dc.contributor.author | Taylor, James | |
dc.date.accessioned | 2022-09-09T08:30:26Z | |
dc.date.available | 2022-09-09T08:30:26Z | |
dc.date.issued | 2022-10-07 | |
dc.identifier | 281039177 | |
dc.identifier | 9b2d632e-00eb-4279-a698-7be99ae36ec7 | |
dc.identifier | 000859819900001 | |
dc.identifier | 85137897701 | |
dc.identifier.citation | Boyce , G , Musolino , S F , Yang , J , Smith , A D & Taylor , J 2022 , ' Arylboronic acid-catalyzed racemization of secondary and tertiary alcohols ' , The Journal of Organic Chemistry , vol. 87 , no. 19 , pp. 13367-13374 . https://doi.org/10.1021/acs.joc.2c01602 | en |
dc.identifier.issn | 0022-3263 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/118800374 | |
dc.identifier.uri | https://hdl.handle.net/10023/25982 | |
dc.description | Funding: Florida Gulf Coast University; University of St Andrews; UK Engineering and Physical Sciences Research Council - EP/J018139/1, EP/L016419/1, EP/V051423/1; Leverhulme Trust - ECF-2014-005. | en |
dc.description.abstract | The use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Brønsted acid-catalyzed C–O bond cleavage through an achiral carbocation intermediate. | |
dc.format.extent | 8 | |
dc.format.extent | 1725167 | |
dc.language.iso | eng | |
dc.relation.ispartof | The Journal of Organic Chemistry | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Arylboronic acid-catalyzed racemization of secondary and tertiary alcohols | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | The Leverhulme Trust | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | https://doi.org/10.1021/acs.joc.2c01602 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | EP/J018139/1 | en |
dc.identifier.grantnumber | EP/L016419/1 | en |
dc.identifier.grantnumber | ECF-2014-005 | en |
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