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Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency.
Org Biomol Chem. 2010 Mar 21; 8(6):1275-9.OB

Abstract

A series of thiourea-amine bifunctional catalysts have been developed by a rational combination of prolines with cinchona alkaloids, which are connected by a thiourea motif. The catalyst 3a, prepared from L-proline and cinchonidine, was found to be a highly efficient catalyst for the conjugate addition of ketones/aldehydes to a wide range of nitroalkenes (up to 98/2 dr and 96% ee). The privileged cinchonidine backbone and the thiourea motif are essential to the reaction activity and enantioselectivity.

Authors+Show Affiliations

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China. jrchen@mails.ccnu.edu.cnNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

20204193

Citation

Chen, Jia-Rong, et al. "Novel Thiourea-amine Bifunctional Catalysts for Asymmetric Conjugate Addition of Ketones/aldehydes to Nitroalkenes: Rational Structural Combination for High Catalytic Efficiency." Organic & Biomolecular Chemistry, vol. 8, no. 6, 2010, pp. 1275-9.
Chen JR, Cao YJ, Zou YQ, et al. Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency. Org Biomol Chem. 2010;8(6):1275-9.
Chen, J. R., Cao, Y. J., Zou, Y. Q., Tan, F., Fu, L., Zhu, X. Y., & Xiao, W. J. (2010). Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency. Organic & Biomolecular Chemistry, 8(6), 1275-9. https://doi.org/10.1039/b925962g
Chen JR, et al. Novel Thiourea-amine Bifunctional Catalysts for Asymmetric Conjugate Addition of Ketones/aldehydes to Nitroalkenes: Rational Structural Combination for High Catalytic Efficiency. Org Biomol Chem. 2010 Mar 21;8(6):1275-9. PubMed PMID: 20204193.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency. AU - Chen,Jia-Rong, AU - Cao,Yi-Ju, AU - Zou,You-Quan, AU - Tan,Fen, AU - Fu,Liang, AU - Zhu,Xiao-Yu, AU - Xiao,Wen-Jing, Y1 - 2010/01/21/ PY - 2010/3/6/entrez PY - 2010/3/6/pubmed PY - 2010/6/10/medline SP - 1275 EP - 9 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 8 IS - 6 N2 - A series of thiourea-amine bifunctional catalysts have been developed by a rational combination of prolines with cinchona alkaloids, which are connected by a thiourea motif. The catalyst 3a, prepared from L-proline and cinchonidine, was found to be a highly efficient catalyst for the conjugate addition of ketones/aldehydes to a wide range of nitroalkenes (up to 98/2 dr and 96% ee). The privileged cinchonidine backbone and the thiourea motif are essential to the reaction activity and enantioselectivity. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/20204193/Novel_thiourea_amine_bifunctional_catalysts_for_asymmetric_conjugate_addition_of_ketones/aldehydes_to_nitroalkenes:_rational_structural_combination_for_high_catalytic_efficiency_ L2 - https://doi.org/10.1039/b925962g DB - PRIME DP - Unbound Medicine ER -