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Article: A concise asymmetric route to chiral α-aminoxy acids

TitleA concise asymmetric route to chiral α-aminoxy acids
Authors
KeywordsΑ-Aminoxy Acid
Aldehydes
Alkynes
Asymmetric Synthesis
Mitsunobu Reaction
Issue Date2009
PublisherGeorg Thieme Verlag. The Journal's web site is located at http://www.thieme-chemistry.com/thieme-chemistry/journals/info/synlett/index.shtml
Citation
Synlett, 2009 n. 19, p. 3159-3162 How to Cite?
AbstractAn efficient three-step method has been developed for enantioselective synthesis of chiral α-aminoxy acids from, aldehydes. In this method, chiral propargylic alcohols are obtained by asymmetric addition of terminal alkynes to aldehydes. The hydroxyl group then converted to aminoxy group via Mitsunobu reaction and oxidative cleavage of the internal carbon - carbon triple bond produce the carboxylic acid group. This represents a convenient approach to the general asymmetric synthesis of α-aminoxy acids with the advantages of substantial overall yields (37-73%) and high enantioselectivities (81-99% ee). © Georg Thieme Verlag Stuttgart.
Persistent Identifierhttp://hdl.handle.net/10722/168418
ISSN
2015 Impact Factor: 2.323
2015 SCImago Journal Rankings: 0.908
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorChang, XWen_US
dc.contributor.authorZhang, DWen_US
dc.contributor.authorChen, Fen_US
dc.contributor.authorDong, ZMen_US
dc.contributor.authorYang, Den_US
dc.date.accessioned2012-10-08T03:18:43Z-
dc.date.available2012-10-08T03:18:43Z-
dc.date.issued2009en_US
dc.identifier.citationSynlett, 2009 n. 19, p. 3159-3162en_US
dc.identifier.issn0936-5214en_US
dc.identifier.urihttp://hdl.handle.net/10722/168418-
dc.description.abstractAn efficient three-step method has been developed for enantioselective synthesis of chiral α-aminoxy acids from, aldehydes. In this method, chiral propargylic alcohols are obtained by asymmetric addition of terminal alkynes to aldehydes. The hydroxyl group then converted to aminoxy group via Mitsunobu reaction and oxidative cleavage of the internal carbon - carbon triple bond produce the carboxylic acid group. This represents a convenient approach to the general asymmetric synthesis of α-aminoxy acids with the advantages of substantial overall yields (37-73%) and high enantioselectivities (81-99% ee). © Georg Thieme Verlag Stuttgart.en_US
dc.languageengen_US
dc.publisherGeorg Thieme Verlag. The Journal's web site is located at http://www.thieme-chemistry.com/thieme-chemistry/journals/info/synlett/index.shtmlen_US
dc.relation.ispartofSynletten_US
dc.subjectΑ-Aminoxy Aciden_US
dc.subjectAldehydesen_US
dc.subjectAlkynesen_US
dc.subjectAsymmetric Synthesisen_US
dc.subjectMitsunobu Reactionen_US
dc.titleA concise asymmetric route to chiral α-aminoxy acidsen_US
dc.typeArticleen_US
dc.identifier.emailYang, D:yangdan@hku.hken_US
dc.identifier.authorityYang, D=rp00825en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1055/s-0029-1218306en_US
dc.identifier.scopuseid_2-s2.0-72049114415en_US
dc.identifier.hkuros180938-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-72049114415&selection=ref&src=s&origin=recordpageen_US
dc.identifier.issue19en_US
dc.identifier.spage3159en_US
dc.identifier.epage3162en_US
dc.identifier.isiWOS:000273254600019-
dc.publisher.placeGermanyen_US
dc.identifier.scopusauthoridChang, XW=35319791100en_US
dc.identifier.scopusauthoridZhang, DW=35320759400en_US
dc.identifier.scopusauthoridChen, F=7404908085en_US
dc.identifier.scopusauthoridDong, ZM=7402274471en_US
dc.identifier.scopusauthoridYang, D=7404800756en_US

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