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Article: Highly Enantioselective Synthesis Using Prolinol as Chiral Auxiliary. Silver-Mediated Synthesis of Axially Chiral Vinylallenes and Subsequent (Hetero)-Diels-Alder Reactions

TitleHighly Enantioselective Synthesis Using Prolinol as Chiral Auxiliary. Silver-Mediated Synthesis of Axially Chiral Vinylallenes and Subsequent (Hetero)-Diels-Alder Reactions
Authors
Lo, KYChan, YMZhou, DToy, PHChe, CM
Issue Date2019
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html
Citation
Organic Letters, 2019, v. 21 n. 19, p. 7717-7721 How to Cite?
DOI: http://dx.doi.org/10.1021/acs.orglett.9b02514
AbstractUsing (S)-prolinol as a chiral auxiliary, axially chiral vinylallenes with excellent enantiopurity (up to >99% enantiomeric excess (ee)) were readily prepared from optically pure propargylamines in the presence of AgNO3 under microwave irradiation. Subsequent (hetero)-Diels-Alder reaction of these axially chiral vinylallenes with azodicarboxylates or maleimides on water demonstrates excellent axial-to-point chirality transfer (up to 99% ee). Copyright © 2019 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/278116
ISSN
1523-7060
2021 Impact Factor: 6.072
2020 SCImago Journal Rankings: 1.940
ISI Accession Number ID
WOS:000489200100007

 

DC FieldValueLanguage
dc.contributor.authorLo, KY-
dc.contributor.authorChan, YM-
dc.contributor.authorZhou, D-
dc.contributor.authorToy, PH-
dc.contributor.authorChe, CM-
dc.date.accessioned2019-10-04T08:07:48Z-
dc.date.available2019-10-04T08:07:48Z-
dc.date.issued2019-
dc.identifier.citationOrganic Letters, 2019, v. 21 n. 19, p. 7717-7721-
dc.identifier.issn1523-7060-
dc.identifier.urihttp://hdl.handle.net/10722/278116-
dc.description.abstractUsing (S)-prolinol as a chiral auxiliary, axially chiral vinylallenes with excellent enantiopurity (up to >99% enantiomeric excess (ee)) were readily prepared from optically pure propargylamines in the presence of AgNO3 under microwave irradiation. Subsequent (hetero)-Diels-Alder reaction of these axially chiral vinylallenes with azodicarboxylates or maleimides on water demonstrates excellent axial-to-point chirality transfer (up to 99% ee). Copyright © 2019 American Chemical Society.-
dc.languageeng-
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html-
dc.relation.ispartofOrganic Letters-
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in [JournalTitle], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html].-
dc.titleHighly Enantioselective Synthesis Using Prolinol as Chiral Auxiliary. Silver-Mediated Synthesis of Axially Chiral Vinylallenes and Subsequent (Hetero)-Diels-Alder Reactions-
dc.typeArticle-
dc.identifier.emailLo, KY: vkylo@hku.hk-
dc.identifier.emailToy, PH: phtoy@hkucc.hku.hk-
dc.identifier.emailChe, CM: chemhead@hku.hk-
dc.identifier.authorityToy, PH=rp00791-
dc.identifier.authorityChe, CM=rp00670-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/acs.orglett.9b02514-
dc.identifier.pmid31553194-
dc.identifier.scopuseid_2-s2.0-85072943519-
dc.identifier.hkuros306172-
dc.identifier.volume21-
dc.identifier.issue19-
dc.identifier.spage7717-
dc.identifier.epage7721-
dc.identifier.isiWOS:000489200100007-
dc.publisher.placeUnited States-
dc.identifier.issnl1523-7052-

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