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Xie JB, Luo J, Winn TR, et al. Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines. Beilstein J Org Chem. 2014;10:746-51doi: 10.3762/bjoc.10.69.
Xie, 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, 10746-51. https://doi.org/10.3762/bjoc.10.69
Xie, Jian-Bo, et al. "Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines." Beilstein journal of organic chemistry vol. 10 (2014): 746-51. doi: https://doi.org/10.3762/bjoc.10.69
Xie JB, Luo J, Winn TR, Cordes DB, Li G. Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines. Beilstein J Org Chem. 2014 Mar 31;10:746-51. doi: 10.3762/bjoc.10.69. eCollection 2014. PMID: 24778728; PMCID: PMC3999766.
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Beilstein J Org Chem. 2014 Mar 31;10:746-51. doi: 10.3762/bjoc.10.69. eCollection 2014.

Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines.

Beilstein journal of organic chemistry

Jian-Bo Xie, Jian Luo, Timothy R Winn, David B Cordes, Guigen Li

Affiliations

  1. Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, United States.
  2. Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, United States ; Institute of Chemistry & BioMedical Sciences (ICBMS), Nanjing University, Nanjing 210093, P. R. China.

PMID: 24778728 PMCID: PMC3999766 DOI: 10.3762/bjoc.10.69

Abstract

A 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.

Keywords: GAP chemistry; N-phosphinylimine; Velcade; asymmetric borylation; organophosphorous

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