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Conference Paper: Reductive aldol cyclizations of unsaturated thioester derivatives of 1,3-cyclopentanedione catalyzed by chiral copper hydrides

TitleReductive aldol cyclizations of unsaturated thioester derivatives of 1,3-cyclopentanedione catalyzed by chiral copper hydrides
Authors
KeywordsAldol reaction
Copper
Cyclization
Enantioselective catalysis
Reduction
Issue Date2012
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
Citation
Tetrahedron, 2012, v. 68 n. 17, p. 3450-3456 How to Cite?
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.
Persistent Identifierhttp://hdl.handle.net/10722/159326
ISSN
2015 Impact Factor: 2.645
2015 SCImago Journal Rankings: 0.991
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorOu, Jen_HK
dc.contributor.authorWong, WTen_HK
dc.contributor.authorChiu, Pen_HK
dc.date.accessioned2012-08-16T05:48:40Z-
dc.date.available2012-08-16T05:48:40Z-
dc.date.issued2012en_HK
dc.identifier.citationTetrahedron, 2012, v. 68 n. 17, p. 3450-3456en_HK
dc.identifier.issn0040-4020en_HK
dc.identifier.urihttp://hdl.handle.net/10722/159326-
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.en_HK
dc.languageengen_US
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/teten_HK
dc.relation.ispartofTetrahedronen_HK
dc.subjectAldol reactionen_HK
dc.subjectCopperen_HK
dc.subjectCyclizationen_HK
dc.subjectEnantioselective catalysisen_HK
dc.subjectReductionen_HK
dc.titleReductive aldol cyclizations of unsaturated thioester derivatives of 1,3-cyclopentanedione catalyzed by chiral copper hydridesen_HK
dc.typeConference_Paperen_HK
dc.identifier.emailWong, WT: wtwong@hku.hken_HK
dc.identifier.emailChiu, P: pchiu@hku.hken_HK
dc.identifier.authorityWong, WT=rp00811en_HK
dc.identifier.authorityChiu, P=rp00680en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/j.tet.2011.07.057en_HK
dc.identifier.scopuseid_2-s2.0-84859533910en_HK
dc.identifier.hkuros203937en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-84859533910&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume68en_HK
dc.identifier.issue17en_HK
dc.identifier.spage3450en_HK
dc.identifier.epage3456en_HK
dc.identifier.isiWOS:000303303300009-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridOu, J=35234687200en_HK
dc.identifier.scopusauthoridWong, WT=7403973084en_HK
dc.identifier.scopusauthoridChiu, P=11140148700en_HK
dc.identifier.citeulike10533857-

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