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Chiral phosphoproline-catalyzed asymmetric Michael addition of ketones to nitroolefins: an experimental and theoretical study.
Org Biomol Chem. 2011 Oct 21; 9(20):6973-8.OB

Abstract

A novel pyrrolidine-based chiral phosphoproline is an effective bifunctional organocatalyst for the asymmetric Michael addition of ketones to nitroolefins giving high levels of diastereo- and enantio-selectivities (up to > 99 : 1 dr and 96% ee). anti-SR Transition state has the lowest barrier which controls the stereoselectivity, in agreement with experimental results.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zeng Z
Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, P. R. China.
Luo P
No affiliation info available
Jiang Y
No affiliation info available
Liu Y
No affiliation info available
Tang G
No affiliation info available
Xu P
No affiliation info available
Zhao Y
No affiliation info available
Blackburn GM
No affiliation info available

MeSH

AlkenesCatalysisKetonesMolecular StructureNitro CompoundsPhosphorylationProlineStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21863184

Citation

Zeng, Zhiping, et al. "Chiral Phosphoproline-catalyzed Asymmetric Michael Addition of Ketones to Nitroolefins: an Experimental and Theoretical Study." Organic & Biomolecular Chemistry, vol. 9, no. 20, 2011, pp. 6973-8.
Zeng Z, Luo P, Jiang Y, et al. Chiral phosphoproline-catalyzed asymmetric Michael addition of ketones to nitroolefins: an experimental and theoretical study. Org Biomol Chem. 2011;9(20):6973-8.
Zeng, Z., Luo, P., Jiang, Y., Liu, Y., Tang, G., Xu, P., Zhao, Y., & Blackburn, G. M. (2011). Chiral phosphoproline-catalyzed asymmetric Michael addition of ketones to nitroolefins: an experimental and theoretical study. Organic & Biomolecular Chemistry, 9(20), 6973-8. https://doi.org/10.1039/c1ob06143g
Zeng Z, et al. Chiral Phosphoproline-catalyzed Asymmetric Michael Addition of Ketones to Nitroolefins: an Experimental and Theoretical Study. Org Biomol Chem. 2011 Oct 21;9(20):6973-8. PubMed PMID: 21863184.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chiral phosphoproline-catalyzed asymmetric Michael addition of ketones to nitroolefins: an experimental and theoretical study. AU - Zeng,Zhiping, AU - Luo,Ping, AU - Jiang,Yao, AU - Liu,Yan, AU - Tang,Guo, AU - Xu,Pengxiang, AU - Zhao,Yufen, AU - Blackburn,G Michael, Y1 - 2011/08/24/ PY - 2011/8/25/entrez PY - 2011/8/25/pubmed PY - 2012/1/4/medline SP - 6973 EP - 8 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 9 IS - 20 N2 - A novel pyrrolidine-based chiral phosphoproline is an effective bifunctional organocatalyst for the asymmetric Michael addition of ketones to nitroolefins giving high levels of diastereo- and enantio-selectivities (up to > 99 : 1 dr and 96% ee). anti-SR Transition state has the lowest barrier which controls the stereoselectivity, in agreement with experimental results. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/21863184/Chiral_phosphoproline_catalyzed_asymmetric_Michael_addition_of_ketones_to_nitroolefins:_an_experimental_and_theoretical_study_ L2 - https://doi.org/10.1039/c1ob06143g DB - PRIME DP - Unbound Medicine ER -