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Asymmetric direct aldol reaction of functionalized ketones catalyzed by amine organocatalysts based on bispidine.
J Am Chem Soc. 2008 Apr 30; 130(17):5654-5.JA

Abstract

Organocatalysts containing primary-secondary amine based on bispidine and amino acid have been designed to catalyze the asymmetric direct aldol reaction of functionalized ketones including alpha-keto phosphonates, alpha-keto esters, as well as alpha,alpha-dialkoxy ketones as aldol reaction acceptors. The corresponding products with chiral tertiary alcohols were obtained in moderate to high yields (up to 97%) and high enantioselectivities (up to 98% ee). A theoretical study of transition structures demonstrated that protonated piperidine was important for the reactivity and enantioselectivity of this reaction.

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Authors+Show Affiliations

Liu J
Key Laboratory of Green Chemistry & Technology, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
Yang Z
No affiliation info available
Wang Z
No affiliation info available
Wang F
No affiliation info available
Chen X
No affiliation info available
Liu X
No affiliation info available
Feng X
No affiliation info available
Su Z
No affiliation info available
Hu C
No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18380434

Citation

Liu, Jie, et al. "Asymmetric Direct Aldol Reaction of Functionalized Ketones Catalyzed By Amine Organocatalysts Based On Bispidine." Journal of the American Chemical Society, vol. 130, no. 17, 2008, pp. 5654-5.
Liu J, Yang Z, Wang Z, et al. Asymmetric direct aldol reaction of functionalized ketones catalyzed by amine organocatalysts based on bispidine. J Am Chem Soc. 2008;130(17):5654-5.
Liu, J., Yang, Z., Wang, Z., Wang, F., Chen, X., Liu, X., Feng, X., Su, Z., & Hu, C. (2008). Asymmetric direct aldol reaction of functionalized ketones catalyzed by amine organocatalysts based on bispidine. Journal of the American Chemical Society, 130(17), 5654-5. https://doi.org/10.1021/ja800839w
Liu J, et al. Asymmetric Direct Aldol Reaction of Functionalized Ketones Catalyzed By Amine Organocatalysts Based On Bispidine. J Am Chem Soc. 2008 Apr 30;130(17):5654-5. PubMed PMID: 18380434.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric direct aldol reaction of functionalized ketones catalyzed by amine organocatalysts based on bispidine. AU - Liu,Jie, AU - Yang,Zhigang, AU - Wang,Zhen, AU - Wang,Fei, AU - Chen,Xiaohong, AU - Liu,Xiaohua, AU - Feng,Xiaoming, AU - Su,Zhishan, AU - Hu,Changwei, Y1 - 2008/04/02/ PY - 2008/4/3/pubmed PY - 2008/4/3/medline PY - 2008/4/3/entrez SP - 5654 EP - 5 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 130 IS - 17 N2 - Organocatalysts containing primary-secondary amine based on bispidine and amino acid have been designed to catalyze the asymmetric direct aldol reaction of functionalized ketones including alpha-keto phosphonates, alpha-keto esters, as well as alpha,alpha-dialkoxy ketones as aldol reaction acceptors. The corresponding products with chiral tertiary alcohols were obtained in moderate to high yields (up to 97%) and high enantioselectivities (up to 98% ee). A theoretical study of transition structures demonstrated that protonated piperidine was important for the reactivity and enantioselectivity of this reaction. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/18380434/Asymmetric_direct_aldol_reaction_of_functionalized_ketones_catalyzed_by_amine_organocatalysts_based_on_bispidine_ DB - PRIME DP - Unbound Medicine ER -