Journal
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES
Volume 34, Issue 1, Pages 84-89Publisher
HIGHER EDUCATION PRESS
DOI: 10.1007/s40242-018-7189-z
Keywords
Asymmetric Michael addition; (1R,2R)-(+)-1,2-DPEN; Immobilization; Enantioselectivity
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Funding
- National Natural Science Foundation of China [21476163]
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Two Wang resin-supported (1R,2R)-(+)-1,2-DPEN(DPEN=diphenylethyle nediamine) catalysts were synthesized from cyanuric chloride and trimesoyl chloride, respectively. These two catalysts were characterized by FTIR, TGA and elemental analysis. The results demonstrated that (1R,2R)-(+)-1,2-DPEN was successfully bonded to the surface of Wang resin through the amido linkage. Subsequently, the asymmetric Michael addition of acetone to beta-nitrostyrene was employed to evaluate their catalytic performance. It was found that the catalyst generated from trimesoyl chloride exhibited much better catalytic behavior than our previously reported catalyst, likely attributed to the multiple hydrogen-bond interaction between beta-nitrostyrene and amide group, which made the catalytic transition intermediates more stable. Under the optimal conditions, 76.1% beta-nitrostyrene conversion and 93.8% enantioselectivity were obtained. Finally, the generality of this catalyst was examined with Michael additions of acetone to beta-nitroolefins and excellent enantioselectivities(91.9% to 99.9%) were achieved.
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