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Direct asymmetric Michael addition of thioether-based aryl sulfanyl-propan-2-one to nitroalkenes catalyzed by a chiral amine-thiourea bifunctional organocatalyst.
Chirality. 2010 Jul; 22(7):625-34.C

Abstract

Although the organocatalytic direct asymmetric Michael reactions of carbonyl compounds to nitroalkenes have been investigated intensely, the Michael reaction of the thioether-based donors remains a rather undeveloped field. This work concerns the asymmetric Michael addition of aryl sulfanyl-propan-2-one to nitroalkenes with benzoic acid as an additive, and chiral amine-thiourea as a bifunctional organocatalyst. The reactions provided the highly functionalized chiral adducts with excellent enantioselectivities (up to 96% ee) and good yields. Moreover, the further transformed products exhibited excellent diastereoselectivity.

Authors+Show Affiliations

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China.No 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

20143410

Citation

Jiang, Xianxing, et al. "Direct Asymmetric Michael Addition of Thioether-based Aryl Sulfanyl-propan-2-one to Nitroalkenes Catalyzed By a Chiral Amine-thiourea Bifunctional Organocatalyst." Chirality, vol. 22, no. 7, 2010, pp. 625-34.
Jiang X, Zhang B, Zhang Y, et al. Direct asymmetric Michael addition of thioether-based aryl sulfanyl-propan-2-one to nitroalkenes catalyzed by a chiral amine-thiourea bifunctional organocatalyst. Chirality. 2010;22(7):625-34.
Jiang, X., Zhang, B., Zhang, Y., Lin, L., Yan, W., & Wang, R. (2010). Direct asymmetric Michael addition of thioether-based aryl sulfanyl-propan-2-one to nitroalkenes catalyzed by a chiral amine-thiourea bifunctional organocatalyst. Chirality, 22(7), 625-34. https://doi.org/10.1002/chir.20689
Jiang X, et al. Direct Asymmetric Michael Addition of Thioether-based Aryl Sulfanyl-propan-2-one to Nitroalkenes Catalyzed By a Chiral Amine-thiourea Bifunctional Organocatalyst. Chirality. 2010;22(7):625-34. PubMed PMID: 20143410.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct asymmetric Michael addition of thioether-based aryl sulfanyl-propan-2-one to nitroalkenes catalyzed by a chiral amine-thiourea bifunctional organocatalyst. AU - Jiang,Xianxing, AU - Zhang,Bangzhi, AU - Zhang,Yifu, AU - Lin,Li, AU - Yan,Wenjin, AU - Wang,Rui, PY - 2010/2/10/entrez PY - 2010/2/10/pubmed PY - 2010/8/27/medline SP - 625 EP - 34 JF - Chirality JO - Chirality VL - 22 IS - 7 N2 - Although the organocatalytic direct asymmetric Michael reactions of carbonyl compounds to nitroalkenes have been investigated intensely, the Michael reaction of the thioether-based donors remains a rather undeveloped field. This work concerns the asymmetric Michael addition of aryl sulfanyl-propan-2-one to nitroalkenes with benzoic acid as an additive, and chiral amine-thiourea as a bifunctional organocatalyst. The reactions provided the highly functionalized chiral adducts with excellent enantioselectivities (up to 96% ee) and good yields. Moreover, the further transformed products exhibited excellent diastereoselectivity. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/20143410/Direct_asymmetric_Michael_addition_of_thioether_based_aryl_sulfanyl_propan_2_one_to_nitroalkenes_catalyzed_by_a_chiral_amine_thiourea_bifunctional_organocatalyst_ L2 - https://doi.org/10.1002/chir.20689 DB - PRIME DP - Unbound Medicine ER -
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