A New Valuable Synthesis of Polyfunctionalized Furans Starting from β-Nitroenones and Active Methylene Compounds.

A New Valuable Synthesis of Polyfunctionalized Furans Starting from β-Nitroenones and Active Methylene Compounds.

Molecules (Basel, Switzerland) (2019-12-19)

Elena Chiurchiù, Serena Gabrielli, Roberto Ballini, Alessandro Palmieri

ABSTRACT

Highly functionalized furans are the key scaffolds of many pharmaceuticals and bioactive natural products. Herein, we disclose a new fruitful synthesis of polyfunctionalized furans starting from β-nitroenones and α-functionalized ketones. The protocol involves two steps promoted by solid supported species, and it provides the title targets from satisfactory to very good overall yields and in an excellent diastereomeric ratios.

MATERIALS

Product Number

Brand

Product Description

20026

Sigma-Aldrich

2-tert-Butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene, extent of labeling: ~2.2 mmol/g base loading

47060

Sigma-Aldrich

Fluoride on polymer support, extent of labeling: ~3.0 mmol/g F^- loading

39410

Sigma-Aldrich

4-(Dimethylamino)pyridine, polymer-bound, extent of labeling: ~3.0 mmol/g "DMAP" loading, matrix crosslinked with 2% DVB