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.
Links
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 -