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.
Links
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 -