Group-Assisted Purification (GAP) Chemistry for the Synthesis of Velcade via Asymmetric Borylation of N-Phosphinylimines

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dc.creatorXie, Jian Bo (TTU)
dc.creatorLuo, Jian (TTU)
dc.creatorWinn, Timothy R. (TTU)
dc.creatorCordes, David B. (TTU)
dc.creatorLi, Guigen (TTU)
dc.date.accessioned2023-09-13T18:58:54Z
dc.date.available2023-09-13T18:58:54Z
dc.date.issued2014
dc.descriptioncc-by
dc.description.abstractA new approach to the anticancer drug Velcade was developed by performing asymmetric borylation of an imine anchored with a chiral N-phosphinyl auxiliary. Throughout the 7-step synthesis, especially in the imine's synthesis and in the asymmetric borylation reactions, operations and work-up were conducted in simple and easy ways without any column chromatographic purification, which defines the GAP (group-assisted purification) chemistry concept. It was found that the optically pure isomer (dr > 99:1) can be readily obtained by washing the crude mixture of the asymmetric borylation reaction with hexane; the chiral N-phosphinyl auxiliary can be easily recovered after deprotection is finished. Several other N-phosphinylimines were also investigated for the asymmetric borylation reaction. The absolute configuration of the borylation product was confirmed by single crystal X-ray diffraction analysis.© 2014 Xie et al.
dc.identifier.citationXie, J.-B., Luo, J., Winn, T.R., Cordes, D.B., & Li, G.. 2014. Group-Assisted Purification (GAP) Chemistry for the Synthesis of Velcade via Asymmetric Borylation of N-Phosphinylimines. Beilstein Journal of Organic Chemistry, 10. https://doi.org/10.3762/bjoc.10.69
dc.identifier.urihttps://doi.org/10.3762/bjoc.10.69
dc.identifier.urihttps://hdl.handle.net/2346/96038
dc.language.isoeng
dc.subjectAsymmetric borylation
dc.subjectGAP chemistry
dc.subjectN-phosphinylimine
dc.subjectOrganophosphorous
dc.subjectVelcade
dc.titleGroup-Assisted Purification (GAP) Chemistry for the Synthesis of Velcade via Asymmetric Borylation of N-Phosphinylimines
dc.typeArticle

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