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Contra-thermodynamic, photocatalytic E→Z isomerization of styrenyl boron species : vectors to facilitate exploration of two-dimensional chemical space
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dc.contributor.author | Molloy, John J. | |
dc.contributor.author | Metternich, Jan B. | |
dc.contributor.author | Daniliuc, Constantin G. | |
dc.contributor.author | Watson, Allan J. B. | |
dc.contributor.author | Gilmour, Ryan | |
dc.date.accessioned | 2019-02-21T00:33:47Z | |
dc.date.available | 2019-02-21T00:33:47Z | |
dc.date.issued | 2018-03-12 | |
dc.identifier | 252373767 | |
dc.identifier | d015d995-7b10-4f08-aea0-cfc017eb44ee | |
dc.identifier | 85042222326 | |
dc.identifier | 000426759900028 | |
dc.identifier.citation | Molloy , J J , Metternich , J B , Daniliuc , C G , Watson , A J B & Gilmour , R 2018 , ' Contra -thermodynamic, photocatalytic E→Z isomerization of styrenyl boron species : vectors to facilitate exploration of two-dimensional chemical space ' , Angewandte Chemie International Edition , vol. 57 , no. 12 , pp. 3168-3172 . https://doi.org/10.1002/anie.201800286 | en |
dc.identifier.issn | 1521-3773 | |
dc.identifier.other | Bibtex: urn:2a5d921f304bc963d0fce69c2ed0467d | |
dc.identifier.other | ORCID: /0000-0002-1582-4286/work/56639189 | |
dc.identifier.uri | https://hdl.handle.net/10023/17112 | |
dc.description | We acknowledge financial support from the WWU Münster, Deutsche Forschungsgemeinschaft (Excellence Cluster EXC 1003), and Fonds der Chemischen Industrie (Fellowship to JBM). JJM was supported by a PEER/PECRE award by WestChem and the Scottish Funding Council. | en |
dc.description.abstract | Designing strategies to access stereodefined olefinic organoboron species is an important synthetic challenge. Despite significant advances, there is a striking paucity of routes to Z-α-substituted styrenyl organoborons. Herein, this strategic imbalance is redressed by exploiting the polarity of the C(sp2)−B bond to activate the neighboring π system, thus enabling a mild, traceless photocatalytic isomerization of readily accessible E-α-substituted styrenyl BPins to generate the corresponding Z-isomers with high fidelity. Preliminary validation of this contra-thermodynamic E→Z isomerization is demonstrated in a series of stereoretentive transformations to generate Z-configured trisubstituted alkenes, as well as in a concise synthesis of the anti-tumor agent Combretastatin A4. | |
dc.format.extent | 1502420 | |
dc.language.iso | eng | |
dc.relation.ispartof | Angewandte Chemie International Edition | en |
dc.subject | Alkenes | en |
dc.subject | Boron | en |
dc.subject | Conformational analysis | en |
dc.subject | Isomerizations | en |
dc.subject | Natural products | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Contra-thermodynamic, photocatalytic E→Z isomerization of styrenyl boron species : vectors to facilitate exploration of two-dimensional chemical space | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | 10.1002/anie.201800286 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2019-02-21 |
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