The highly enantioselective bifunctional organocatalysts for the Michael addition of сyclohexanone to titroolefins
- Authors: Yang M.1, Zhang Y.C.1, Zhao J.Q.1, Yang Q.S.1, Ma Y.2, Cao X.H.1
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Affiliations:
- School of Chemical Engineering and Technology
- National Key Laboratory of Elemento-Organic Chemistry
- Issue: Vol 86, No 6 (2016)
- Pages: 1381-1388
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/215361
- DOI: https://doi.org/10.1134/S1070363216060244
- ID: 215361
Cite item
Abstract
A new family of organocatalyst derived from proline has been developed and shown to be an efficient catalyst for asymmetric Michael addition of cyclohexanone to nitroolefins with high diastereo- and enanthio -selectivities. (syn: anti ratio up to 99:1, ee. up to 95%.). The result of computational studies at the B3LYP/6-31G* level indicate that both the hydrogen bonding and the stereo hindrance play the crucial role in the activation of the nitro alkene and help to discriminate between the two diastereofacial approaches.
Keywords
About the authors
M. Yang
School of Chemical Engineering and Technology
Email: nkallwar@126.com
China, Tianjin
Y. C. Zhang
School of Chemical Engineering and Technology
Email: nkallwar@126.com
China, Tianjin
J. Q. Zhao
School of Chemical Engineering and Technology
Email: nkallwar@126.com
China, Tianjin
Q. S. Yang
School of Chemical Engineering and Technology
Email: nkallwar@126.com
China, Tianjin
Y. Ma
National Key Laboratory of Elemento-Organic Chemistry
Email: nkallwar@126.com
China, Tianjin
X. H. Cao
School of Chemical Engineering and Technology
Author for correspondence.
Email: nkallwar@126.com
China, Tianjin