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- Publisher Website: 10.1021/acs.orglett.9b02514
- Scopus: eid_2-s2.0-85072943519
- PMID: 31553194
- WOS: WOS:000489200100007
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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
Title | Highly Enantioselective Synthesis Using Prolinol as Chiral Auxiliary. Silver-Mediated Synthesis of Axially Chiral Vinylallenes and Subsequent (Hetero)-Diels-Alder Reactions |
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Authors | |
Issue Date | 2019 |
Publisher | American 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? |
Abstract | Using (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 Identifier | http://hdl.handle.net/10722/278116 |
ISSN | 2023 Impact Factor: 4.9 2023 SCImago Journal Rankings: 1.245 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Lo, KY | - |
dc.contributor.author | Chan, YM | - |
dc.contributor.author | Zhou, D | - |
dc.contributor.author | Toy, PH | - |
dc.contributor.author | Che, CM | - |
dc.date.accessioned | 2019-10-04T08:07:48Z | - |
dc.date.available | 2019-10-04T08:07:48Z | - |
dc.date.issued | 2019 | - |
dc.identifier.citation | Organic Letters, 2019, v. 21 n. 19, p. 7717-7721 | - |
dc.identifier.issn | 1523-7060 | - |
dc.identifier.uri | http://hdl.handle.net/10722/278116 | - |
dc.description.abstract | Using (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.language | eng | - |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html | - |
dc.relation.ispartof | Organic Letters | - |
dc.rights | This 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.title | Highly Enantioselective Synthesis Using Prolinol as Chiral Auxiliary. Silver-Mediated Synthesis of Axially Chiral Vinylallenes and Subsequent (Hetero)-Diels-Alder Reactions | - |
dc.type | Article | - |
dc.identifier.email | Lo, KY: vkylo@hku.hk | - |
dc.identifier.email | Toy, PH: phtoy@hkucc.hku.hk | - |
dc.identifier.email | Che, CM: chemhead@hku.hk | - |
dc.identifier.authority | Toy, PH=rp00791 | - |
dc.identifier.authority | Che, CM=rp00670 | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/acs.orglett.9b02514 | - |
dc.identifier.pmid | 31553194 | - |
dc.identifier.scopus | eid_2-s2.0-85072943519 | - |
dc.identifier.hkuros | 306172 | - |
dc.identifier.volume | 21 | - |
dc.identifier.issue | 19 | - |
dc.identifier.spage | 7717 | - |
dc.identifier.epage | 7721 | - |
dc.identifier.isi | WOS:000489200100007 | - |
dc.publisher.place | United States | - |
dc.identifier.issnl | 1523-7052 | - |