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Article: Desymmetrizing reductive aldol cyclizations of enethioate derivatives of 1,3-diones catalyzed by a chiral copper hydride

TitleDesymmetrizing reductive aldol cyclizations of enethioate derivatives of 1,3-diones catalyzed by a chiral copper hydride
Authors
Issue Date2012
PublisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/obc
Citation
Organic And Biomolecular Chemistry, 2012, v. 10 n. 30, p. 5971-5978 How to Cite?
AbstractA range of enethioate derivatives of 1,3-diones underwent reductive aldol cyclizations catalyzed by a chiral copper hydride generated in situ from 5 mol% TaniaPhos (SL-T001-1), 5 mol% Cu(OAc) 2·H 2O, 5 mol% bipyridine and 2.0 equiv. of PhSiH 3, to furnish polycyclic β-hydroxythioester products bearing three newly established contiguous stereocenters, with >98:2 dr and in up to 94% yield and 98% ee. The use of an amine such as bipyridine or 2,6-lutidine as additive results in an increase of the overall reaction rate. The major bicyclic aldol product has all substituents cis and can be rationalized by a reductively generated (Z)-enolate reacting with the dione via a cyclic transition state. © 2012 The Royal Society of Chemistry.
Persistent Identifierhttp://hdl.handle.net/10722/168655
ISSN
2015 Impact Factor: 3.559
2015 SCImago Journal Rankings: 1.464
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorOu, Jen_US
dc.contributor.authorWong, WTen_US
dc.contributor.authorChiu, Pen_US
dc.date.accessioned2012-10-08T03:24:02Z-
dc.date.available2012-10-08T03:24:02Z-
dc.date.issued2012en_US
dc.identifier.citationOrganic And Biomolecular Chemistry, 2012, v. 10 n. 30, p. 5971-5978en_US
dc.identifier.issn1477-0520en_US
dc.identifier.urihttp://hdl.handle.net/10722/168655-
dc.description.abstractA range of enethioate derivatives of 1,3-diones underwent reductive aldol cyclizations catalyzed by a chiral copper hydride generated in situ from 5 mol% TaniaPhos (SL-T001-1), 5 mol% Cu(OAc) 2·H 2O, 5 mol% bipyridine and 2.0 equiv. of PhSiH 3, to furnish polycyclic β-hydroxythioester products bearing three newly established contiguous stereocenters, with >98:2 dr and in up to 94% yield and 98% ee. The use of an amine such as bipyridine or 2,6-lutidine as additive results in an increase of the overall reaction rate. The major bicyclic aldol product has all substituents cis and can be rationalized by a reductively generated (Z)-enolate reacting with the dione via a cyclic transition state. © 2012 The Royal Society of Chemistry.en_US
dc.languageengen_US
dc.publisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/obcen_US
dc.relation.ispartofOrganic and Biomolecular Chemistryen_US
dc.titleDesymmetrizing reductive aldol cyclizations of enethioate derivatives of 1,3-diones catalyzed by a chiral copper hydrideen_US
dc.typeArticleen_US
dc.identifier.emailChiu, P:pchiu@hku.hken_US
dc.identifier.authorityChiu, P=rp00680en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1039/c2ob25206fen_US
dc.identifier.pmid22576882-
dc.identifier.scopuseid_2-s2.0-84863895736en_US
dc.identifier.hkuros205782-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-84863895736&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume10en_US
dc.identifier.issue30en_US
dc.identifier.spage5971en_US
dc.identifier.epage5978en_US
dc.identifier.isiWOS:000306276800045-
dc.publisher.placeUnited Kingdomen_US
dc.identifier.scopusauthoridOu, J=35234687200en_US
dc.identifier.scopusauthoridWong, WT=35932584500en_US
dc.identifier.scopusauthoridChiu, P=11140148700en_US

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