Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza-Heterocycles.

Llona-Minguez S, Desroses M, Ghassemian A, Jacques SA, Eriksson L, Isacksson R, Koolmeister T, Stenmark P, Scobie M, Helleday T

Chemistry 21 (20) 7394-7398 [2015-05-11; online 2015-03-25]

A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a "metal-free" nitrene insertion, resulting in a new pyrrole ring. This novel synthetic approach has a wide substrate tolerance and it is applicable in the preparation of more complex "drug-like" molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic β-aminophosphonate motif.

Affiliated researcher

PubMed 25809883

DOI 10.1002/chem.201406549

Crossref 10.1002/chem.201406549

Publications 9.5.0