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Assessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanine
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dc.contributor.author | D'Hollander, Agathe C. A. | |
dc.contributor.author | Westwood, Nicholas J. | |
dc.date.accessioned | 2018-11-16T00:48:18Z | |
dc.date.available | 2018-11-16T00:48:18Z | |
dc.date.issued | 2018-01-11 | |
dc.identifier | 251552506 | |
dc.identifier | cd797763-f047-4ac0-8c97-1abb4c36ccc4 | |
dc.identifier | 85036500463 | |
dc.identifier | 000423248700002 | |
dc.identifier.citation | D'Hollander , A C A & Westwood , N J 2018 , ' Assessment of the regioselectivity in the condensation reaction of unsymmetrical o -phthaldialdehydes with alanine ' , Tetrahedron , vol. 74 , no. 2 , pp. 224-239 . https://doi.org/10.1016/j.tet.2017.11.035 | en |
dc.identifier.issn | 0040-4020 | |
dc.identifier.other | RIS: urn:1BE25EBD8F659F32AB9608F653F476B6 | |
dc.identifier.other | ORCID: /0000-0003-0630-0138/work/56424145 | |
dc.identifier.uri | https://hdl.handle.net/10023/16480 | |
dc.description | Funding: We would like to thank the EPSRC DTG at the University of St Andrews for funding. | en |
dc.description.abstract | One approach for the synthesis of isoindolinones, a privileged bioactive heterocyclic core structure, involves a condensation reaction of o-phthaldialdehydes with a suitable nitrogen-containing nucleophile. This fascinating reaction is revisited here in the context of the use of o-phthaldialdehydes that contain additional substituents in the aromatic ring leading to a detailed analysis of the regioselectivity of the reaction. Eleven monosubstituted o-phthaldialdehydes were synthesised and reacted with alanine. The regioselectivity observed across the eleven substrates led to the design of a disubstituted substrate that reacted with very high control. A gram-scale reaction followed by esterification gave one major regioisomer in high yield. In addition, the regioselectivity observed on reaction of two novel monodeuterated substrates led to an increased mechanistic understanding. | |
dc.format.extent | 1768939 | |
dc.language.iso | eng | |
dc.relation.ispartof | Tetrahedron | en |
dc.subject | o-phthaldialdehyde | en |
dc.subject | Condensation reaction | en |
dc.subject | Regioselectivity | en |
dc.subject | Mechanistic understanding | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | Assessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanine | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | 10.1016/j.tet.2017.11.035 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2018-11-16 | |
dc.identifier.url | http://www.sciencedirect.com/science/article/pii/S0040402017311833#appd001 | en |
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