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Asymmetric iodoamination of chalcones and 4-aryl-4-oxobutenoates catalyzed by a complex based on scandium(III) and a N,N'-dioxide ligand.
Chemistry. 2011 Dec 23; 17(52):14916-21.C

Abstract

Highly diastereo- and enantioselective iodoamination of chalcones, 4-aryl-4-oxobutenoates, and a trifluoro-substituted enone has been accomplished in the presence of a chiral N,N'-dioxide/[Sc(OTf)(3)] complex (0.5-2 mol%), delivering the desired vicinal anti-α-iodo-β-amino carbonyl compounds regioselectively in high yields (up to 97%) and with excellent diastereoselectivities (>99:1 d.r.) and enantioselectivities (up to 99% ee). Enantiopure syn-α-iodo-β-amino products could also be obtained from the isomerization of particular iodo compounds. TsNHX species (X=Cl, Br, I), generated from the reactions between the halo sources and TsNH(2), were further confirmed as the active species in the haloamination reactions involved in the formation of the key halonium ion intermediates. A typical haloamination dependency was observed, with reactivity decreasing in the order NBS>NIS≫NCS.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Cai Y
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China.
Liu X
No affiliation info available
Li J
No affiliation info available
Chen W
No affiliation info available
Wang W
No affiliation info available
Lin L
No affiliation info available
Feng X
No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

22161911

Citation

Cai, Yunfei, et al. "Asymmetric Iodoamination of Chalcones and 4-aryl-4-oxobutenoates Catalyzed By a Complex Based On scandium(III) and a N,N'-dioxide Ligand." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 17, no. 52, 2011, pp. 14916-21.
Cai Y, Liu X, Li J, et al. Asymmetric iodoamination of chalcones and 4-aryl-4-oxobutenoates catalyzed by a complex based on scandium(III) and a N,N'-dioxide ligand. Chemistry. 2011;17(52):14916-21.
Cai, Y., Liu, X., Li, J., Chen, W., Wang, W., Lin, L., & Feng, X. (2011). Asymmetric iodoamination of chalcones and 4-aryl-4-oxobutenoates catalyzed by a complex based on scandium(III) and a N,N'-dioxide ligand. Chemistry (Weinheim an Der Bergstrasse, Germany), 17(52), 14916-21. https://doi.org/10.1002/chem.201102453
Cai Y, et al. Asymmetric Iodoamination of Chalcones and 4-aryl-4-oxobutenoates Catalyzed By a Complex Based On scandium(III) and a N,N'-dioxide Ligand. Chemistry. 2011 Dec 23;17(52):14916-21. PubMed PMID: 22161911.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric iodoamination of chalcones and 4-aryl-4-oxobutenoates catalyzed by a complex based on scandium(III) and a N,N'-dioxide ligand. AU - Cai,Yunfei, AU - Liu,Xiaohua, AU - Li,Jun, AU - Chen,Weiliang, AU - Wang,Wentao, AU - Lin,Lili, AU - Feng,Xiaoming, Y1 - 2011/12/08/ PY - 2011/08/08/received PY - 2011/12/14/entrez PY - 2011/12/14/pubmed PY - 2011/12/14/medline SP - 14916 EP - 21 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 17 IS - 52 N2 - Highly diastereo- and enantioselective iodoamination of chalcones, 4-aryl-4-oxobutenoates, and a trifluoro-substituted enone has been accomplished in the presence of a chiral N,N'-dioxide/[Sc(OTf)(3)] complex (0.5-2 mol%), delivering the desired vicinal anti-α-iodo-β-amino carbonyl compounds regioselectively in high yields (up to 97%) and with excellent diastereoselectivities (>99:1 d.r.) and enantioselectivities (up to 99% ee). Enantiopure syn-α-iodo-β-amino products could also be obtained from the isomerization of particular iodo compounds. TsNHX species (X=Cl, Br, I), generated from the reactions between the halo sources and TsNH(2), were further confirmed as the active species in the haloamination reactions involved in the formation of the key halonium ion intermediates. A typical haloamination dependency was observed, with reactivity decreasing in the order NBS>NIS≫NCS. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/22161911/Asymmetric_iodoamination_of_chalcones_and_4_aryl_4_oxobutenoates_catalyzed_by_a_complex_based_on_scandium_III__and_a_NN'_dioxide_ligand_ L2 - https://doi.org/10.1002/chem.201102453 DB - PRIME DP - Unbound Medicine ER -