(1R,2R)-(+)-(1,2)-DPEN-Bonded Sulfonic Acid Resin: A Trifunctional Heterogeneous Catalyst for Asymmetric Michael Additions of Acetone to Nitroolefins

Abstract

Based on (1R,2R)-(+)-(1,2)-DPEN skeleton, a series of primary amine–sulfamide bifunctional catalysts were synthesized, which exhibited excellent catalytic performance in the Michael addition of acetone to β-nitrostyrene. Therefore, a trifunctional heterogeneous catalyst was designed and prepared by simple N-sulfonyl reaction of (1R,2R)-(+)-(1,2)-DPEN and sulfonyl chloride resin. It was employed for the aforementioned addition without any additive and satisfactory results (80.5% conversion; 84.3% ee) were obtained. Meanwhile, the structural and textural properties of the catalyst were characterized by infrared spectroscopy (FT-IR), elemental analysis, SEM, and N₂ adsorption and desorption experiments. Finally, the generality of the catalyst was investigated.

GRAPHICAL ABSTRACT

Keywords:

• (1R,2R)-(+)-(1,2)-DPEN
• Asymmetric catalysis
• Michael addition
• trifunctional heterogeneous catalyst

SUPPLEMENTAL MATERIAL

General information on experimental details, HRMS and ¹H and ¹³C NMR data of catalysts 1a–1d and the Michael adducts, the details of HPLC analysis conditions, and the HPLC spectra of the Michael adducts for this article can be accessed on the publisher’s website.