1312815-41-0Relevant articles and documents
Oxalyl Boronates Enable Modular Synthesis of Bioactive Imidazoles
Lee, C. Frank,Holownia, Aleksandra,Bennett, James M.,Elkins, Jonathan M.,St. Denis, Jeffrey D.,Adachi, Shinya,Yudin, Andrei K.
, p. 6264 - 6267 (2017/05/19)
Described herein is the preparation of oxalyl boronate building blocks and their application for the construction of heterocycles. The oxalyl unit, readily accessible through commercially available starting materials, enables a modular approach for the synthesis of imidazoles. A variety of aromatic, heteroaromatic, and alkyl carboxaldehydes were condensed with oxalyl boronates to afford substituted boryl imidazoles in a regiocontrolled fashion. Subsequent palladium-catalyzed cross-coupling with haloarenes furnished the desired trisubstituted imidazole scaffolds. To demonstrate the utility of these scaffolds, potent inhibitors of the serine/threonine-protein kinase STK10 were synthesized.
(1-Bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis Dedicated to Professor Paul Wender with deepest admiration on his receipt of the 2012 Tetrahedron Prize for Creativity in Organic Chemistry
Woerly, Eric M.,Miller, Jonathan E.,Burke, Martin D.
, p. 7732 - 7740 (2013/08/23)
Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, (1-bromovinyl)-N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as a starting material for the preparation of a wide range of 1,1-disubstituted olefin-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various 1,1-disubstituted olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform.
