schliessen

Filtern

 

Bibliotheken

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 N,N'-dioxide/[Sc(OTf) sub(3)] complex (0.5-2mol%), delivering the desired vicinal anti- alpha -iodo- beta -amino carbonyl com... Full description

Journal Title: Chemistry: A European Journal 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
Link: http://search.proquest.com/docview/1800495032/?pq-origsite=primo
Zum Text:
SendSend as email Add to Book BagAdd to Book Bag
Staff View
recordid: proquest1800495032
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:
  • Halos
  • Formations
  • Asymmetry
  • Isomerization
  • Ligands
  • Carbonyl Compounds
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, 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 N,N'-dioxide/[Sc(OTf) sub(3)] complex (0.5-2mol%), delivering the desired vicinal anti- alpha -iodo- beta -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- alpha -iodo- beta -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 sub(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>NISNCS. Highly diastereo- and enantioselective 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 super(III) and a N,N'-dioxide ligand (0.5-2mol%) has been developed. This method delivers the desired vicinal anti- alpha -iodo- beta -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:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


@attributes
ID645161667
RANK0.07
NO1
SEARCH_ENGINEprimo_central_multiple_fe
SEARCH_ENGINE_TYPEPrimo Central Search Engine
LOCALfalse
PrimoNMBib
record
control
sourcerecordid1800495032
sourceidproquest
recordidTN_proquest1800495032
sourcesystemOther
pqid1800495032
display
typearticle
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
contributorCai, Yunfei (correspondence author)
ispartofChemistry: A European Journal, December 2011, Vol.17(52), pp.14916-14921
identifier
subjectHalos ; Formations ; Asymmetry ; Isomerization ; Ligands ; Carbonyl Compounds ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
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 N,N'-dioxide/[Sc(OTf) sub(3)] complex (0.5-2mol%), delivering the desired vicinal anti- alpha -iodo- beta -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- alpha -iodo- beta -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 sub(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>NISNCS. Highly diastereo- and enantioselective 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 super(III) and a N,N'-dioxide ligand (0.5-2mol%) has been developed. This method delivers the desired vicinal anti- alpha -iodo- beta -amino products regioselectively with excellent yields and enantioselectivity (see scheme).
languageeng
source
version6
lds50peer_reviewed
links
openurl$$Topenurl_article
openurlfulltext$$Topenurlfull_article
backlink$$Uhttp://search.proquest.com/docview/1800495032/?pq-origsite=primo$$EView_record_in_ProQuest_(subscribers_only)
search
creatorcontrib
0Cai, Yunfei
1Liu, Xiaohua
2Li, Jun
3Chen, Weiliang
4Wang, Wentao
5Lin, Lili
6Feng, Xiaoming
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 N,N'-dioxide/[Sc(OTf) sub(3)] complex (0.5-2mol%), delivering the desired vicinal anti- alpha -iodo- beta -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- alpha -iodo- beta -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 sub(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>NISNCS. Highly diastereo- and enantioselective 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 super(III) and a N,N'-dioxide ligand (0.5-2mol%) has been developed. This method delivers the desired vicinal anti- alpha -iodo- beta -amino products regioselectively with excellent yields and enantioselectivity (see scheme).
subject
0Halos
1Formations
2Asymmetry
3Isomerization
4Ligands
5Carbonyl Compounds
6Analysis (MD)
7Chemical Analysis (Ep)
8Chemical Analysis (Ed)
9Chemical Analysis (EC)
1023
11B3
general
0English
110.1002/chem.201102453
2Engineered Materials Abstracts
3METADEX
4Materials Research Database
5Technology Research Database
6ProQuest Materials Science Collection
7ProQuest Technology Collection
8ProQuest SciTech Collection
9Materials Science & Engineering Database
10SciTech Premium Collection
11Technology Collection
sourceidproquest
recordidproquest1800495032
issn
009476539
10947-6539
215213765
31521-3765
rsrctypearticle
creationdate2011
addtitleChemistry: A European Journal
searchscope
01007393
11007528
21007944
310000014
410000015
510000022
610000049
710000053
810000120
910000201
1010000203
1110000209
1210000250
1310000260
1410000265
15proquest
scope
01007393
11007528
21007944
310000014
410000015
510000022
610000049
710000053
810000120
910000201
1010000203
1110000209
1210000250
1310000260
1410000265
15proquest
lsr43
01007393false
11007528false
21007944false
310000014false
410000015false
510000022false
610000049false
710000053false
810000120false
910000201false
1010000203false
1110000209false
1210000250false
1310000260false
1410000265false
contributorCai, Yunfei
startdate20111201
enddate20111201
citationpf 14916 pt 14921 vol 17 issue 52
lsr30VSR-Enriched:[date, pqid]
sort
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
creationdate20111201
lso0120111201
facets
frbrgroupid7092820440683957004
frbrtype5
languageeng
creationdate2011
topic
0Halos
1Formations
2Asymmetry
3Isomerization
4Ligands
5Carbonyl Compounds
6Analysis (MD)
7Chemical Analysis (Ep)
8Chemical Analysis (Ed)
9Chemical Analysis (EC)
collection
0Engineered Materials Abstracts
1METADEX
2Materials Research Database
3Technology Research Database
4ProQuest Materials Science Collection
5ProQuest Technology Collection
6ProQuest SciTech Collection
7Materials Science & Engineering Database
8SciTech Premium Collection
9Technology Collection
prefilterarticles
rsrctypearticles
creatorcontrib
0Cai, Yunfei
1Liu, Xiaohua
2Li, Jun
3Chen, Weiliang
4Wang, Wentao
5Lin, Lili
6Feng, Xiaoming
jtitleChemistry: A European Journal
toplevelpeer_reviewed
delivery
delcategoryRemote Search Resource
fulltextfulltext
addata
aulast
0Cai
1Liu
2Li
3Chen
4Wang
5Lin
6Feng
aufirst
0Yunfei
1Xiaohua
2Jun
3Weiliang
4Wentao
5Lili
6Xiaoming
au
0Cai, Yunfei
1Liu, Xiaohua
2Li, Jun
3Chen, Weiliang
4Wang, Wentao
5Lin, Lili
6Feng, Xiaoming
addauCai, Yunfei
atitleAsymmetric Iodoamination of Chalcones and 4-Aryl-4-oxobutenoates Catalyzed by a Complex Based on Scandium(III) and a N,N'-Dioxide Ligand
jtitleChemistry: A European Journal
risdate20111201
volume17
issue52
spage14916
epage14921
pages14916-14921
issn0947-6539
eissn1521-3765
formatjournal
genrearticle
ristypeJOUR
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 N,N'-dioxide/[Sc(OTf) sub(3)] complex (0.5-2mol%), delivering the desired vicinal anti- alpha -iodo- beta -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- alpha -iodo- beta -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 sub(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>NISNCS. Highly diastereo- and enantioselective 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 super(III) and a N,N'-dioxide ligand (0.5-2mol%) has been developed. This method delivers the desired vicinal anti- alpha -iodo- beta -amino products regioselectively with excellent yields and enantioselectivity (see scheme).
doi10.1002/chem.201102453
urlhttp://search.proquest.com/docview/1800495032/
date2011-12-23