Synthesis and Utility of Dihydropyridine Boronic Esters

Abstract

When activated by an acylating agent, pyridine boronic esters react with organometallic reagents to form ad ihydropyridine boronic ester.T his intermediate allows access to an umber of valuable substituted pyridine,d ihydropyridine,and piperidine products.

Lewis Acid Catalyzed Stereoselective Dearomative Coupling of Indolylboron Ate Complexes with Donor–Acceptor Cyclopropanes and Alkyl Halides

“…[1] Boron reagents [2] have attracted particular attention along those lines.F or example,t he research groups of Aggarwal [3] and Ready [4] developed at hree-component dearomative coupling of pyridines via their 4-pyridylboron ate complexes induced by N-acylation involving a1 ,2-metalate rearrangement. [1] Boron reagents [2] have attracted particular attention along those lines.F or example,t he research groups of Aggarwal [3] and Ready [4] developed at hree-component dearomative coupling of pyridines via their 4-pyridylboron ate complexes induced by N-acylation involving a1 ,2-metalate rearrangement.…”

“…Multicomponent coupling reactions are highly valuable for the modular construction of complex organic compounds. [1] Boron reagents [2] have attracted particular attention along those lines.F or example,t he research groups of Aggarwal [3] and Ready [4] developed at hree-component dearomative coupling of pyridines via their 4-pyridylboron ate complexes induced by N-acylation involving a1 ,2-metalate rearrangement. Aggarwal and co-workers recently described an elegant coupling of 2-lithiofuran with various boronic esters as induced by trifluoromethyl radical addition (Scheme 1A).…”