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A Direct Phosphine-Mediated Synthesis of Pyrroles from Acid Chlorides and α,β-Unsaturated Imines

Yingdong Lu and Bruce A. Arndtsen*

*Department of Chemistry, McGill University, 801 Sherbrooke Street W., Montreal QC H3A 2K6, Canada, Email: bruce.arndtsenmcgill.ca

Y. Lu, B. A. Arndtsen, Org. Lett., 2009, 11, 1369-1372.

DOI: 10.1021/ol900185n (free Supporting Information)


Abstract

A one-step reaction to assemble pyrroles from α,β-unsaturated imines and acid chlorides is mediated by triphenylphosphine, which eliminates phosphine oxide to allow cyclization. This reaction has been employed to access broad range of pyrroles via modulation of the two building blocks and applied as well to the synthesis of Lukianol A.

see article for more examples

Lukianol A


proposed mechanism



Key Words

Pyrroles, Triphenylphosphine


ID: J54-Y2009-0900