Allylated β-Ketoesters as Precursors in Paal-Knorr-Type Pyrrole Synthesis: Preparations of Chiral and Bispyrroles

Abstract

A simple and facile preparation of chiral and bis-pyrroles is described here. This method involves a modified Paal-Knorr reaction using 1,4-dicarbonyl systems derived from ozonolysis of allylated β-ketoester.

Paal-Knorr synthesis - chiral and bispyrroles - ozonolysis - allylated β-ketoester

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<A NAME="RM00604SS-14">14</A>

Solvents such as MeOH, CH₃CN, THF, EtOAc, CH₂Cl₂, and toluene were screened with CH₃CN giving the highest yield and cleanest products as determined by LCMS. The reactions were also run at r.t., 50 °C, and 80 °C to determine the optimal temperature. A variety of acids such as aq HCl and aq H₂SO₄were screened in addition to p-TsOH.