Chiral copper-salen complex grafted over functionalized mesoporous silica as an efficient catalyst for asymmetric Henry reactions and synthesis of the potent drug (R)-isoproterenol. (21st June 2018)

• Record Type: Journal Article
• Authors: Halder, Mita; Bhanja, Piyali; Islam, Md. Mominul; Bhaumik, Asim; Islam, Sk. Manirul
• Is Part Of: New journal of chemistry. Volume 42:Number 14(2018)
• Page Start: 11896
• Page End: 11904
• Publication Date: 2018-06-21
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c8nj01745j
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : A new chiral Cu(ii )@AFS-1 catalyzed asymmetric Henry reaction (ee = 94%, yield 96%) and diastereoselective Henry reaction have been reported. Additionally, drug ( R )-(−)-isoproterenol was synthesized using this protocol. Abstract : Synthesis of enantiomerically pure drug molecules using functionalized mesoporous materials bearing a chiral moiety is a longstanding goal in heterogeneous catalysis. Herein, we report an efficient and enantioselective one-pot Henry reaction over a highly ordered functionalized mesoporous silica-supported chiral copper-salen catalyst, Cu(ii )@AFS-1, in DCM at RT. The catalyst was characterized by UV-Vis, FT-IR spectroscopy, PXRD, N2 adsorption/desorption, HR-TEM, EPR, and thermogravimetric and elemental analyses. The diastereoselective Henry reaction of nitroethane was carried out by using this catalyst to obtain good yields (up to 96%) and ee (up to 95%) of β-nitroalcohols with acceptable dr (3.2 : 1). Additionally, the enantiomerically pure drug ( R )-(−)-isoproterenol can be synthesized through the asymmetric Henry reaction of 3, 4-dimethoxybenzaldehyde over this chiral mesoporous Cu-catalyst as a key step.