schliessen

Filtern

 

Bibliotheken

Enantioselective cross-coupling of meso-epoxides with aryl halides

The first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-β-arylcycloalkanols is presented. The reaction is catalyzed by a combination of (bpy)NiCl2 and a chiral titanocene under reducing conditions. Yields range from 57 to 99% with 78-95% enantiomeric... Full description

Journal Title: Journal of the American Chemical Society 11 March 2015, Vol.137(9), pp.3237-40
Main Author: Zhao, Yang
Other Authors: Weix, Daniel J
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-5126 ; PMID: 25716775 Version:1 ; DOI: 10.1021/jacs.5b01909
Link: http://pubmed.gov/25716775
Zum Text:
SendSend as email Add to Book BagAdd to Book Bag
Staff View
recordid: medline25716775
title: Enantioselective cross-coupling of meso-epoxides with aryl halides
format: Article
creator:
  • Zhao, Yang
  • Weix, Daniel J
subjects:
  • Epoxy Compounds -- Chemistry
ispartof: Journal of the American Chemical Society, 11 March 2015, Vol.137(9), pp.3237-40
description: The first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-β-arylcycloalkanols is presented. The reaction is catalyzed by a combination of (bpy)NiCl2 and a chiral titanocene under reducing conditions. Yields range from 57 to 99% with 78-95% enantiomeric excess. The 30 examples include a variety of functional groups (ether, ester, ketone, nitrile, ketal, trifluoromethyl, sulfonamide, sulfonate ester), both aryl and vinyl halides, and five- to seven-membered rings. The intermediacy of a carbon radical is strongly suggested by the conversion of cyclooctene monoxide to an aryl [3.3.0]bicyclooctanol.
language: eng
source:
identifier: E-ISSN: 1520-5126 ; PMID: 25716775 Version:1 ; DOI: 10.1021/jacs.5b01909
fulltext: fulltext
issn:
  • 15205126
  • 1520-5126
url: Link


@attributes
ID761913200
RANK0.07
NO1
SEARCH_ENGINEprimo_central_multiple_fe
SEARCH_ENGINE_TYPEPrimo Central Search Engine
LOCALfalse
PrimoNMBib
record
control
sourcerecordid25716775
sourceidmedline
recordidTN_medline25716775
sourceformatXML
sourcesystemPC
pqid1662638448
display
typearticle
titleEnantioselective cross-coupling of meso-epoxides with aryl halides
creatorZhao, Yang ; Weix, Daniel J
ispartofJournal of the American Chemical Society, 11 March 2015, Vol.137(9), pp.3237-40
identifier
subjectEpoxy Compounds -- Chemistry
descriptionThe first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-β-arylcycloalkanols is presented. The reaction is catalyzed by a combination of (bpy)NiCl2 and a chiral titanocene under reducing conditions. Yields range from 57 to 99% with 78-95% enantiomeric excess. The 30 examples include a variety of functional groups (ether, ester, ketone, nitrile, ketal, trifluoromethyl, sulfonamide, sulfonate ester), both aryl and vinyl halides, and five- to seven-membered rings. The intermediacy of a carbon radical is strongly suggested by the conversion of cyclooctene monoxide to an aryl [3.3.0]bicyclooctanol.
languageeng
source
version5
lds50peer_reviewed
links
openurl$$Topenurl_article
backlink$$Uhttp://pubmed.gov/25716775$$EView_this_record_in_MEDLINE/PubMed
openurlfulltext$$Topenurlfull_article
addlink$$Uhttp://exlibris-pub.s3.amazonaws.com/aboutMedline.html$$EView_the_MEDLINE/PubMed_Copyright_Statement
search
creatorcontrib
0Zhao, Yang
1Weix, Daniel J
titleEnantioselective cross-coupling of meso-epoxides with aryl halides
descriptionThe first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-β-arylcycloalkanols is presented. The reaction is catalyzed by a combination of (bpy)NiCl2 and a chiral titanocene under reducing conditions. Yields range from 57 to 99% with 78-95% enantiomeric excess. The 30 examples include a variety of functional groups (ether, ester, ketone, nitrile, ketal, trifluoromethyl, sulfonamide, sulfonate ester), both aryl and vinyl halides, and five- to seven-membered rings. The intermediacy of a carbon radical is strongly suggested by the conversion of cyclooctene monoxide to an aryl [3.3.0]bicyclooctanol.
subjectEpoxy Compounds -- Chemistry
general
025716775
1English
2MEDLINE/PubMed (U.S. National Library of Medicine)
310.1021/jacs.5b01909
4MEDLINE/PubMed (NLM)
sourceidmedline
recordidmedline25716775
issn
015205126
11520-5126
rsrctypearticle
creationdate2015
addtitleJournal of the American Chemical Society
searchscope
0medline
1nlm_medline
2MEDLINE
scope
0medline
1nlm_medline
2MEDLINE
lsr4120150311
citationpf 3237 vol 137 issue 9
startdate20150311
enddate20150311
lsr30VSR-Enriched:[pqid]
sort
titleEnantioselective cross-coupling of meso-epoxides with aryl halides
authorZhao, Yang ; Weix, Daniel J
creationdate20150311
lso0120150311
facets
frbrgroupid8986116948054246929
frbrtype5
newrecords20190701
languageeng
creationdate2015
topicEpoxy Compounds–Chemistry
collectionMEDLINE/PubMed (NLM)
prefilterarticles
rsrctypearticles
creatorcontrib
0Zhao, Yang
1Weix, Daniel J
jtitleJournal Of The American Chemical Society
toplevelpeer_reviewed
delivery
delcategoryRemote Search Resource
fulltextfulltext
addata
aulast
0Zhao
1Weix
aufirst
0Yang
1Daniel J
au
0Zhao, Yang
1Weix, Daniel J
atitleEnantioselective cross-coupling of meso-epoxides with aryl halides
jtitleJournal of the American Chemical Society
risdate20150311
volume137
issue9
spage3237
pages3237-40
issn0002-7863
eissn1520-5126
formatjournal
genrearticle
ristypeJOUR
abstractThe first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-β-arylcycloalkanols is presented. The reaction is catalyzed by a combination of (bpy)NiCl2 and a chiral titanocene under reducing conditions. Yields range from 57 to 99% with 78-95% enantiomeric excess. The 30 examples include a variety of functional groups (ether, ester, ketone, nitrile, ketal, trifluoromethyl, sulfonamide, sulfonate ester), both aryl and vinyl halides, and five- to seven-membered rings. The intermediacy of a carbon radical is strongly suggested by the conversion of cyclooctene monoxide to an aryl [3.3.0]bicyclooctanol.
doi10.1021/jacs.5b01909
pmid25716775
date2015-03-11