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2,4-Dinitrophenol as an effective cocatalyst: greatly improving the activities and enantioselectivities of primary amine organocatalysts for asymmetric aldol reactions.
J Org Chem. 2009 Mar 20; 74(6):2541-6.JO

Abstract

Seven primary amine organocatalysts 1a-g were readily prepared from natural primary amino acids via two steps and then were used to catalyze the direct asymmetric aldol reaction, but they showed very poor enantioselectivities and activities. As an effective cocatalyst, 2,4-dinitrophenol (DNP) dramatically elevated the activities and enantioselectivities of these very inefficient primary amine organocatalysts. This remedial course to the very inefficient organocatalysts by selection and employment of the optimal cocatalyst was particularly cost-effective and environment-beneficial compared with de novo development of catalysts. The highest efficient organocatalytic system that was composed of 1f and DNP showed high enantioselectivities and good to high diastereoselectivities with a broad spectrum of seven ketones. The linear ketones and cyclopentanone got predominant syn products whereas cyclohexanone mainly gave anti products.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Da CS
Institute of Biochemistry & Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou 730000, China. dachaoshan@lzu.edu.cn
Che LP
No affiliation info available
Guo QP
No affiliation info available
Wu FC
No affiliation info available
Xiao Ma
No affiliation info available
Jia YN
No affiliation info available

MeSH

2,4-DinitrophenolAlcoholsAldehydesAminesCatalysisCyclohexanonesCyclopentanesKetonesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19249831

Citation

Da, Chao-Shan, et al. "2,4-Dinitrophenol as an Effective Cocatalyst: Greatly Improving the Activities and Enantioselectivities of Primary Amine Organocatalysts for Asymmetric Aldol Reactions." The Journal of Organic Chemistry, vol. 74, no. 6, 2009, pp. 2541-6.
Da CS, Che LP, Guo QP, et al. 2,4-Dinitrophenol as an effective cocatalyst: greatly improving the activities and enantioselectivities of primary amine organocatalysts for asymmetric aldol reactions. J Org Chem. 2009;74(6):2541-6.
Da, C. S., Che, L. P., Guo, Q. P., Wu, F. C., Xiao Ma, ., & Jia, Y. N. (2009). 2,4-Dinitrophenol as an effective cocatalyst: greatly improving the activities and enantioselectivities of primary amine organocatalysts for asymmetric aldol reactions. The Journal of Organic Chemistry, 74(6), 2541-6. https://doi.org/10.1021/jo802758b
Da CS, et al. 2,4-Dinitrophenol as an Effective Cocatalyst: Greatly Improving the Activities and Enantioselectivities of Primary Amine Organocatalysts for Asymmetric Aldol Reactions. J Org Chem. 2009 Mar 20;74(6):2541-6. PubMed PMID: 19249831.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 2,4-Dinitrophenol as an effective cocatalyst: greatly improving the activities and enantioselectivities of primary amine organocatalysts for asymmetric aldol reactions. AU - Da,Chao-Shan, AU - Che,Li-Ping, AU - Guo,Qi-Peng, AU - Wu,Feng-Chun, AU - Xiao Ma,, AU - Jia,Ya-Ning, PY - 2009/3/3/entrez PY - 2009/3/3/pubmed PY - 2009/5/1/medline SP - 2541 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 6 N2 - Seven primary amine organocatalysts 1a-g were readily prepared from natural primary amino acids via two steps and then were used to catalyze the direct asymmetric aldol reaction, but they showed very poor enantioselectivities and activities. As an effective cocatalyst, 2,4-dinitrophenol (DNP) dramatically elevated the activities and enantioselectivities of these very inefficient primary amine organocatalysts. This remedial course to the very inefficient organocatalysts by selection and employment of the optimal cocatalyst was particularly cost-effective and environment-beneficial compared with de novo development of catalysts. The highest efficient organocatalytic system that was composed of 1f and DNP showed high enantioselectivities and good to high diastereoselectivities with a broad spectrum of seven ketones. The linear ketones and cyclopentanone got predominant syn products whereas cyclohexanone mainly gave anti products. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19249831/24_Dinitrophenol_as_an_effective_cocatalyst:_greatly_improving_the_activities_and_enantioselectivities_of_primary_amine_organocatalysts_for_asymmetric_aldol_reactions_ L2 - https://doi.org/10.1021/jo802758b DB - PRIME DP - Unbound Medicine ER -