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Asymmetric Michael reaction of aldehydes with β-nitroalkenes catalyzed by pyrrolidine-camphor derived organocatalysts bearing hydrogen-bond donors.
Chirality. 2012 Apr; 24(4):271-5.C

Abstract

Several pyrrolidine-camphor derived organocatalysts were designed and synthesized. These organocatalysts were used for direct Michael reaction of aldehydes with nitroalkenes to give the desired γ-nitrocarbonyl compounds in high yields (up to 99%), high diastereoselectivities (syn:anti up to 92:8), and good to excellent enantioselectivities (up to 94% ee). Possible transition-state model was also proposed for this asymmetric transformation, which may involve hydrogen-bond interactions between the nucleophilic enamine formed in situ and the nitroalkenes.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Weng J
Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, People's Republic of China.
Ai HB
No affiliation info available
Luo RS
No affiliation info available
Lu G
No affiliation info available

MeSH

AldehydesAlkenesCamphorCatalysisHydrogen BondingModels, ChemicalProlinePyrrolidines

Pub Type(s)

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

Language

eng

PubMed ID

22278901

Citation

Weng, Jiang, et al. "Asymmetric Michael Reaction of Aldehydes With Β-nitroalkenes Catalyzed By Pyrrolidine-camphor Derived Organocatalysts Bearing Hydrogen-bond Donors." Chirality, vol. 24, no. 4, 2012, pp. 271-5.
Weng J, Ai HB, Luo RS, et al. Asymmetric Michael reaction of aldehydes with β-nitroalkenes catalyzed by pyrrolidine-camphor derived organocatalysts bearing hydrogen-bond donors. Chirality. 2012;24(4):271-5.
Weng, J., Ai, H. B., Luo, R. S., & Lu, G. (2012). Asymmetric Michael reaction of aldehydes with β-nitroalkenes catalyzed by pyrrolidine-camphor derived organocatalysts bearing hydrogen-bond donors. Chirality, 24(4), 271-5. https://doi.org/10.1002/chir.21991
Weng J, et al. Asymmetric Michael Reaction of Aldehydes With Β-nitroalkenes Catalyzed By Pyrrolidine-camphor Derived Organocatalysts Bearing Hydrogen-bond Donors. Chirality. 2012;24(4):271-5. PubMed PMID: 22278901.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric Michael reaction of aldehydes with β-nitroalkenes catalyzed by pyrrolidine-camphor derived organocatalysts bearing hydrogen-bond donors. AU - Weng,Jiang, AU - Ai,Hui-Bing, AU - Luo,Ren-Shi, AU - Lu,Gui, Y1 - 2012/01/25/ PY - 2011/07/28/received PY - 2011/12/05/accepted PY - 2012/1/27/entrez PY - 2012/1/27/pubmed PY - 2012/8/29/medline SP - 271 EP - 5 JF - Chirality JO - Chirality VL - 24 IS - 4 N2 - Several pyrrolidine-camphor derived organocatalysts were designed and synthesized. These organocatalysts were used for direct Michael reaction of aldehydes with nitroalkenes to give the desired γ-nitrocarbonyl compounds in high yields (up to 99%), high diastereoselectivities (syn:anti up to 92:8), and good to excellent enantioselectivities (up to 94% ee). Possible transition-state model was also proposed for this asymmetric transformation, which may involve hydrogen-bond interactions between the nucleophilic enamine formed in situ and the nitroalkenes. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/22278901/Asymmetric_Michael_reaction_of_aldehydes_with_β_nitroalkenes_catalyzed_by_pyrrolidine_camphor_derived_organocatalysts_bearing_hydrogen_bond_donors_ L2 - https://doi.org/10.1002/chir.21991 DB - PRIME DP - Unbound Medicine ER -