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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

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 ,‐dioxide/[Sc(OTf)] complex (0.5–2 mol %), delivering the desired vicinal ‐α‐iodo‐β‐amino carbonyl compounds regioselectively... Full description

Journal Title: Chemistry – A European Journal 23 December 2011, Vol.17(52), pp.14916-14921
Main Author: Cai, Yunfei
Other Authors: Liu, Xiaohua , Li, Jun , Chen, Weiliang , Wang, Wentao , Lin, Lili , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201102453
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recordid: wj10.1002/chem.201102453
title: Asymmetric Iodoamination of Chalcones and 4‐Aryl‐4‐oxobutenoates Catalyzed by a Complex Based on Scandium(III) and a N,N′‐Dioxide Ligand
format: Article
creator:
  • Cai, Yunfei
  • Liu, Xiaohua
  • Li, Jun
  • Chen, Weiliang
  • Wang, Wentao
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Asymmetric Catalysis
  • Dioxides
  • Iodoamination
  • Iodonium Ions
  • Scandium
ispartof: Chemistry – A European Journal, 23 December 2011, Vol.17(52), pp.14916-14921
description: 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 ,‐dioxide/[Sc(OTf)] complex (0.5–2 mol %), delivering the desired vicinal ‐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 % ). Enantiopure ‐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, 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. iodoamination of chalcones and 4‐aryl‐4‐oxobutenoates, as well as of a trifluoro‐substituted enone, in the presence of a chiral complex based on Sc and a ,‐dioxide ligand (0.5–2 mol %) has been developed. This method delivers the desired vicinal ‐α‐iodo‐β‐amino products regioselectively with excellent yields and enantioselectivity (see scheme).
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201102453
fulltext: fulltext
issn:
  • 0947-6539
  • 09476539
  • 1521-3765
  • 15213765
url: Link


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titleAsymmetric Iodoamination of Chalcones and 4‐Aryl‐4‐oxobutenoates Catalyzed by a Complex Based on Scandium(III) and a N,N′‐Dioxide Ligand
creatorCai, Yunfei ; Liu, Xiaohua ; Li, Jun ; Chen, Weiliang ; Wang, Wentao ; Lin, Lili ; Feng, Xiaoming
ispartofChemistry – A European Journal, 23 December 2011, Vol.17(52), pp.14916-14921
identifier
subjectAsymmetric Catalysis ; Dioxides ; Iodoamination ; Iodonium Ions ; Scandium
descriptionHighly diastereo‐ and enantioselective iodoamination of chalcones, 4‐aryl‐4‐oxobutenoates, and a trifluoro‐substituted enone has been accomplished in the presence of a chiral ,‐dioxide/[Sc(OTf)] complex (0.5–2 mol %), delivering the desired vicinal ‐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 % ). Enantiopure ‐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, 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. iodoamination of chalcones and 4‐aryl‐4‐oxobutenoates, as well as of a trifluoro‐substituted enone, in the presence of a chiral complex based on Sc and a ,‐dioxide ligand (0.5–2 mol %) has been developed. This method delivers the desired vicinal ‐α‐iodo‐β‐amino products regioselectively with excellent yields and enantioselectivity (see scheme).
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titleAsymmetric Iodoamination of Chalcones and 4‐Aryl‐4‐oxobutenoates Catalyzed by a Complex Based on Scandium(III) and a N,N′‐Dioxide Ligand
descriptionHighly diastereo‐ and enantioselective iodoamination of chalcones, 4‐aryl‐4‐oxobutenoates, and a trifluoro‐substituted enone has been accomplished in the presence of a chiral ,‐dioxide/[Sc(OTf)] complex (0.5–2 mol %), delivering the desired vicinal ‐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 % ). Enantiopure ‐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, 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. iodoamination of chalcones and 4‐aryl‐4‐oxobutenoates, as well as of a trifluoro‐substituted enone, in the presence of a chiral complex based on Sc and a ,‐dioxide ligand (0.5–2 mol %) has been developed. This method delivers the desired vicinal ‐α‐iodo‐β‐amino products regioselectively with excellent yields and enantioselectivity (see scheme).
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titleAsymmetric Iodoamination of Chalcones and 4‐Aryl‐4‐oxobutenoates Catalyzed by a Complex Based on Scandium(III) and a N,N′‐Dioxide Ligand
authorCai, Yunfei ; Liu, Xiaohua ; Li, Jun ; Chen, Weiliang ; Wang, Wentao ; Lin, Lili ; Feng, Xiaoming
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atitleAsymmetric Iodoamination of Chalcones and 4‐Aryl‐4‐oxobutenoates Catalyzed by a Complex Based on Scandium(III) and a N,N′‐Dioxide Ligand
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abstractHighly diastereo‐ and enantioselective iodoamination of chalcones, 4‐aryl‐4‐oxobutenoates, and a trifluoro‐substituted enone has been accomplished in the presence of a chiral ,‐dioxide/[Sc(OTf)] complex (0.5–2 mol %), delivering the desired vicinal ‐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 % ). Enantiopure ‐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, 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. iodoamination of chalcones and 4‐aryl‐4‐oxobutenoates, as well as of a trifluoro‐substituted enone, in the presence of a chiral complex based on Sc and a ,‐dioxide ligand (0.5–2 mol %) has been developed. This method delivers the desired vicinal ‐α‐iodo‐β‐amino products regioselectively with excellent yields and enantioselectivity (see scheme).
copWeinheim
pubWILEY‐VCH Verlag
doi10.1002/chem.201102453
pages14916-14921
date2011-12-23