schliessen

Filtern

 

Bibliotheken

Diastereoselectively Switchable Asymmetric Haloaminocyclization for the Synthesis of Cyclic Sulfamates

An asymmetric synthesis of cyclic sulfamates by catalytic haloaminocyclization of primary sulfamate ester derivatives is described. The remarkable reversal of diastereoselectivity was found to be dependent on the halogen source and the chiral catalyst. By using privileged complexes of N,N'-dioxides... Full description

Journal Title: Chemistry: A European Journal April 2015, Vol.21(17), pp.6386-6389
Main Author: Cai, Yunfei
Other Authors: Zhou, Pengfei , Liu, Xiaohua , Zhao, Jiannan , Lin, Lili , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201500454
Link: http://search.proquest.com/docview/1786204384/?pq-origsite=primo
Zum Text:
SendSend as email Add to Book BagAdd to Book Bag
Staff View
recordid: proquest1786204384
title: Diastereoselectively Switchable Asymmetric Haloaminocyclization for the Synthesis of Cyclic Sulfamates
format: Article
creator:
  • Cai, Yunfei
  • Zhou, Pengfei
  • Liu, Xiaohua
  • Zhao, Jiannan
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Derivatives
  • Halogens
  • Switches
  • Asymmetry
  • Catalysts
  • Synthesis
  • Esters
  • Catalysis
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, April 2015, Vol.21(17), pp.6386-6389
description: An asymmetric synthesis of cyclic sulfamates by catalytic haloaminocyclization of primary sulfamate ester derivatives is described. The remarkable reversal of diastereoselectivity was found to be dependent on the halogen source and the chiral catalyst. By using privileged complexes of N,N'-dioxides with Sc(OTf) sub(3) or Lu(OTf) sub(3) as the catalyst, a variety of enantioenriched syn- and anti-cyclic sulfamates or related trans-aziridines could be obtained in 92-99% ee and up to 97% yield. Switch it up! An asymmetric synthesis of cyclic sulfamates by catalytic haloaminocyclization of primary sulfamate ester derivatives is described. The remarkable reversal of diastereoselectivity was found to be dependent on the halogen source and the chiral catalyst. By using privileged complexes of N,N'-dioxides with Sc(OTf) sub(3) or Lu(OTf) sub(3) as the catalyst, a variety of enantioenriched syn- and anti-cyclic sulfamates could be obtained in excellent results (see scheme).
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201500454
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


@attributes
ID155621605
RANK0.07
NO1
SEARCH_ENGINEprimo_central_multiple_fe
SEARCH_ENGINE_TYPEPrimo Central Search Engine
LOCALfalse
PrimoNMBib
record
control
sourcerecordid1786204384
sourceidproquest
recordidTN_proquest1786204384
sourcesystemOther
pqid1786204384
galeid409040625
display
typearticle
titleDiastereoselectively Switchable Asymmetric Haloaminocyclization for the Synthesis of Cyclic Sulfamates
creatorCai, Yunfei ; Zhou, Pengfei ; Liu, Xiaohua ; Zhao, Jiannan ; Lin, Lili ; Feng, Xiaoming
contributorCai, Yunfei (correspondence author)
ispartofChemistry: A European Journal, April 2015, Vol.21(17), pp.6386-6389
identifier
subjectDerivatives ; Halogens ; Switches ; Asymmetry ; Catalysts ; Synthesis ; Esters ; Catalysis ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionAn asymmetric synthesis of cyclic sulfamates by catalytic haloaminocyclization of primary sulfamate ester derivatives is described. The remarkable reversal of diastereoselectivity was found to be dependent on the halogen source and the chiral catalyst. By using privileged complexes of N,N'-dioxides with Sc(OTf) sub(3) or Lu(OTf) sub(3) as the catalyst, a variety of enantioenriched syn- and anti-cyclic sulfamates or related trans-aziridines could be obtained in 92-99% ee and up to 97% yield. Switch it up! An asymmetric synthesis of cyclic sulfamates by catalytic haloaminocyclization of primary sulfamate ester derivatives is described. The remarkable reversal of diastereoselectivity was found to be dependent on the halogen source and the chiral catalyst. By using privileged complexes of N,N'-dioxides with Sc(OTf) sub(3) or Lu(OTf) sub(3) as the catalyst, a variety of enantioenriched syn- and anti-cyclic sulfamates could be obtained in excellent results (see scheme).
languageeng
source
version8
lds50peer_reviewed
links
openurl$$Topenurl_article
openurlfulltext$$Topenurlfull_article
backlink$$Uhttp://search.proquest.com/docview/1786204384/?pq-origsite=primo$$EView_record_in_ProQuest_(subscribers_only)
search
creatorcontrib
0Cai, Yunfei
1Zhou, Pengfei
2Liu, Xiaohua
3Zhao, Jiannan
4Lin, Lili
5Feng, Xiaoming
titleDiastereoselectively Switchable Asymmetric Haloaminocyclization for the Synthesis of Cyclic Sulfamates
descriptionAn asymmetric synthesis of cyclic sulfamates by catalytic haloaminocyclization of primary sulfamate ester derivatives is described. The remarkable reversal of diastereoselectivity was found to be dependent on the halogen source and the chiral catalyst. By using privileged complexes of N,N'-dioxides with Sc(OTf) sub(3) or Lu(OTf) sub(3) as the catalyst, a variety of enantioenriched syn- and anti-cyclic sulfamates or related trans-aziridines could be obtained in 92-99% ee and up to 97% yield. Switch it up! An asymmetric synthesis of cyclic sulfamates by catalytic haloaminocyclization of primary sulfamate ester derivatives is described. The remarkable reversal of diastereoselectivity was found to be dependent on the halogen source and the chiral catalyst. By using privileged complexes of N,N'-dioxides with Sc(OTf) sub(3) or Lu(OTf) sub(3) as the catalyst, a variety of enantioenriched syn- and anti-cyclic sulfamates could be obtained in excellent results (see scheme).
subject
0Derivatives
1Halogens
2Switches
3Asymmetry
4Catalysts
5Synthesis
6Esters
7Catalysis
8Analysis (MD)
9Chemical Analysis (Ep)
10Chemical Analysis (Ed)
11Chemical Analysis (EC)
1223
13B3
general
0English
110.1002/chem.201500454
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
recordidproquest1786204384
issn
009476539
10947-6539
215213765
31521-3765
rsrctypearticle
creationdate2015
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
startdate20150401
enddate20150401
citationpf 6386 pt 6389 vol 21 issue 17
lsr30VSR-Enriched:[pqid, galeid, date]
sort
titleDiastereoselectively Switchable Asymmetric Haloaminocyclization for the Synthesis of Cyclic Sulfamates
authorCai, Yunfei ; Zhou, Pengfei ; Liu, Xiaohua ; Zhao, Jiannan ; Lin, Lili ; Feng, Xiaoming
creationdate20150401
lso0120150401
facets
frbrgroupid8916394080406688849
frbrtype5
languageeng
creationdate2015
topic
0Derivatives
1Halogens
2Switches
3Asymmetry
4Catalysts
5Synthesis
6Esters
7Catalysis
8Analysis (MD)
9Chemical Analysis (Ep)
10Chemical Analysis (Ed)
11Chemical 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
1Zhou, Pengfei
2Liu, Xiaohua
3Zhao, Jiannan
4Lin, Lili
5Feng, Xiaoming
jtitleChemistry: A European Journal
toplevelpeer_reviewed
delivery
delcategoryRemote Search Resource
fulltextfulltext
addata
aulast
0Cai
1Zhou
2Liu
3Zhao
4Lin
5Feng
aufirst
0Yunfei
1Pengfei
2Xiaohua
3Jiannan
4Lili
5Xiaoming
au
0Cai, Yunfei
1Zhou, Pengfei
2Liu, Xiaohua
3Zhao, Jiannan
4Lin, Lili
5Feng, Xiaoming
addauCai, Yunfei
atitleDiastereoselectively Switchable Asymmetric Haloaminocyclization for the Synthesis of Cyclic Sulfamates
jtitleChemistry: A European Journal
risdate20150401
volume21
issue17
spage6386
epage6389
pages6386-6389
issn0947-6539
eissn1521-3765
formatjournal
genrearticle
ristypeJOUR
abstractAn asymmetric synthesis of cyclic sulfamates by catalytic haloaminocyclization of primary sulfamate ester derivatives is described. The remarkable reversal of diastereoselectivity was found to be dependent on the halogen source and the chiral catalyst. By using privileged complexes of N,N'-dioxides with Sc(OTf) sub(3) or Lu(OTf) sub(3) as the catalyst, a variety of enantioenriched syn- and anti-cyclic sulfamates or related trans-aziridines could be obtained in 92-99% ee and up to 97% yield. Switch it up! An asymmetric synthesis of cyclic sulfamates by catalytic haloaminocyclization of primary sulfamate ester derivatives is described. The remarkable reversal of diastereoselectivity was found to be dependent on the halogen source and the chiral catalyst. By using privileged complexes of N,N'-dioxides with Sc(OTf) sub(3) or Lu(OTf) sub(3) as the catalyst, a variety of enantioenriched syn- and anti-cyclic sulfamates could be obtained in excellent results (see scheme).
doi10.1002/chem.201500454
urlhttp://search.proquest.com/docview/1786204384/
date2015-04-20