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(1R,2R)-(+)-1,2-DPEN-modified Wang resin: An efficient catalyst for the asymmetric Michael addition of acetone to β-nitroolefins

Paper ID Volume ID Publish Year Pages File Format Full-Text
49301 46733 2015 4 PDF Available
Title
(1R,2R)-(+)-1,2-DPEN-modified Wang resin: An efficient catalyst for the asymmetric Michael addition of acetone to β-nitroolefins
Abstract

•Heterogeneous catalyst was achieved via simple N-acylation reaction.•This heterogeneous catalyst presented satisfied results.•The catalytic mechanism was investigated through XPS.•Continuous reaction was realized in a fixed-bed reactor with this catalyst.

Wang resin was modified by (1R,2R)-(+)-1,2-DPEN by means of a triazine ring. The catalyst was characterized by thermogravimetric (TG) analysis, elemental analysis, and Fourier transform infrared spectroscopy (FT-IR). Subsequently, this catalyst was employed for the asymmetric Michael addition of acetone to β-nitrostyrene. Under optimized conditions, 76.6% of β-nitrostyrene conversion and 82.8% enantioselectivity of Michael adduct were obtained. On the basis of the characterization of the catalyst by X-ray photoelectron spectroscopy (XPS), the mechanism of catalysis was proposed. In addition, the generality of the catalyst was evaluated with Michael additions of acetone to β-nitroolefins. Finally, the continuous reaction was realized in a fixed-bed reactor.

Graphical abstractMechanism of Michael addition of acetone to β-nitrostyrene over the catalyst with acetic acid.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Wang resin; (1R,2R)-(+)-1,2-DPEN; Asymmetric Michael addition; Catalytic mechanism; Fixed-bed reactor
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(1R,2R)-(+)-1,2-DPEN-modified Wang resin: An efficient catalyst for the asymmetric Michael addition of acetone to β-nitroolefins
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 71, 5 November 2015, Pages 70–73
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us