Azetidine-Containing Tertiary Boronic Acid Esters

Azetidine-containing tertiary boronic esters (1-4) are useful building blocks for drug discovery researches. Incorporation of azetidine moieties into drug candidates enables improvement of metabolic stability by decreasing lipophilicity and introducing more three-dimensional substructures required by recent trends of drug design.¹⁾
In addition, the pinacol borane moiety can be further converted into a variety of functionalized groups.²⁾ For example, oxidation (a), olefination (b), conversion into trifluoroborate salts (c), an aromatic substitution reaction like the Minisci reaction (d) and visible light photoredox reaction (e) can be applied. Therefore, 1-4 are also good precursors of unique azetidine derivatives.

References

• 1) Multifaceted Substrate-Ligand Interactions Promote the Copper-Catalyzed Hydroboration of Benzylidenecyclobutanes and Related Compounds
  • T. Kang, T. G. Erbay, K. L. Xu, G. M. Gallego, A. Burtea, S. K. Nair, R. L. Patman, R. Zhou, S. C. Sutton, I. J. McAlpine, P. Liu, K. M. Engle, ACS Catal. 2020, 10, 13075.
• 2) Stereospecific functionalizations and transformations of secondary and tertiary boronic esters
  • C. Sandford, V. K. Aggarwal, Chem. Commun. 2017, 53, 5481.

Related Compounds

S0887

Sodium Perborate Tetrahydrate [for Biochemical Research]

I0604

Iodine

P1888

Potassium Hydrogenfluoride

B6161

Ir[dF(CF₃)ppy]₂(bpy)PF₆

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