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Conference Paper: Reductive aldol cyclizations of unsaturated thioester derivatives of 1,3-cyclopentanedione catalyzed by chiral copper hydrides
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TitleReductive aldol cyclizations of unsaturated thioester derivatives of 1,3-cyclopentanedione catalyzed by chiral copper hydrides
 
AuthorsOu, J1
Wong, WT1
Chiu, P1
 
KeywordsAldol reaction
Copper
Cyclization
Enantioselective catalysis
Reduction
 
Issue Date2012
 
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
 
CitationTetrahedron, 2012, v. 68 n. 17, p. 3450-3456 [How to Cite?]
DOI: http://dx.doi.org/10.1016/j.tet.2011.07.057
 
AbstractThe first study on the asymmetric reductive aldol reactions of enethioate derivatives of 1,3-cyclopentanedione showed that 5 mol % of TANIAPHOS (SL-T001-1), and Cu(OAc) 2·H 2O, together with phenylsilane as the stoichiometric reductant, generated the best yields and enantioselectivities of β-hydroxythioester products. With S-benzyl keto-enethioate as substrate, the bicyclo[4.3.0] hydroxythioester product was obtained only as the all-cis diastereomer, in good yield (84%) and enantioselectivity (up to 90% ee). With the related indanedione enethioate derivatives, the reductive aldol cyclization could attain up to 96% ee. These results demonstrate that enethioates have a significantly different reactivity and selectivity profile compared to enoate derivatives in the copper-catalyzed reductive aldol cyclization. © 2011 Elsevier Ltd. All rights reserved.
 
ISSN0040-4020
2013 Impact Factor: 2.817
2013 SCImago Journal Rankings: 1.141
 
DOIhttp://dx.doi.org/10.1016/j.tet.2011.07.057
 
ReferencesReferences in Scopus
 
DC FieldValue
dc.contributor.authorOu, J
 
dc.contributor.authorWong, WT
 
dc.contributor.authorChiu, P
 
dc.date.accessioned2012-08-16T05:48:40Z
 
dc.date.available2012-08-16T05:48:40Z
 
dc.date.issued2012
 
dc.description.abstractThe first study on the asymmetric reductive aldol reactions of enethioate derivatives of 1,3-cyclopentanedione showed that 5 mol % of TANIAPHOS (SL-T001-1), and Cu(OAc) 2·H 2O, together with phenylsilane as the stoichiometric reductant, generated the best yields and enantioselectivities of β-hydroxythioester products. With S-benzyl keto-enethioate as substrate, the bicyclo[4.3.0] hydroxythioester product was obtained only as the all-cis diastereomer, in good yield (84%) and enantioselectivity (up to 90% ee). With the related indanedione enethioate derivatives, the reductive aldol cyclization could attain up to 96% ee. These results demonstrate that enethioates have a significantly different reactivity and selectivity profile compared to enoate derivatives in the copper-catalyzed reductive aldol cyclization. © 2011 Elsevier Ltd. All rights reserved.
 
dc.description.natureLink_to_subscribed_fulltext
 
dc.identifier.citationTetrahedron, 2012, v. 68 n. 17, p. 3450-3456 [How to Cite?]
DOI: http://dx.doi.org/10.1016/j.tet.2011.07.057
 
dc.identifier.citeulike10533857
 
dc.identifier.doihttp://dx.doi.org/10.1016/j.tet.2011.07.057
 
dc.identifier.epage3456
 
dc.identifier.hkuros203937
 
dc.identifier.issn0040-4020
2013 Impact Factor: 2.817
2013 SCImago Journal Rankings: 1.141
 
dc.identifier.issue17
 
dc.identifier.scopuseid_2-s2.0-84859533910
 
dc.identifier.spage3450
 
dc.identifier.urihttp://hdl.handle.net/10722/159326
 
dc.identifier.volume68
 
dc.languageeng
 
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
 
dc.publisher.placeUnited Kingdom
 
dc.relation.ispartofTetrahedron
 
dc.relation.referencesReferences in Scopus
 
dc.subjectAldol reaction
 
dc.subjectCopper
 
dc.subjectCyclization
 
dc.subjectEnantioselective catalysis
 
dc.subjectReduction
 
dc.titleReductive aldol cyclizations of unsaturated thioester derivatives of 1,3-cyclopentanedione catalyzed by chiral copper hydrides
 
dc.typeConference_Paper
 
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Author Affiliations
  1. The University of Hong Kong