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Article: Conjugate reduction and reductive aldol cyclization of α,β- unsaturated thioesters catalyzed by (BDP)CuH

TitleConjugate reduction and reductive aldol cyclization of α,β- unsaturated thioesters catalyzed by (BDP)CuH
Authors
Li, NOu, JMiesch, MChiu, P
Issue Date2011
PublisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/obc
Citation
Organic And Biomolecular Chemistry, 2011, v. 9 n. 17, p. 6143-6147 How to Cite?
DOI: http://dx.doi.org/10.1039/c1ob05352c
AbstractA conjugate reduction of α,β-unsaturated thioesters catalyzed by copper hydride using PMHS as stoichiometric reductant has been developed. 1,2-Bis(diphenylphosphino)benzene (BDP) was the most effective ligand for this reduction. Saturated thioesters could be produced in excellent yields when the substituent on the thiol is not sterically-demanding. This protocol was applied to induce the reductive aldol cyclization of keto-enethioates, which could offer β-hydroxythioesters in moderate to good yields. © 2011 The Royal Society of Chemistry.
Persistent Identifierhttp://hdl.handle.net/10722/135349
ISSN
1477-0520
2021 Impact Factor: 3.890
2020 SCImago Journal Rankings: 0.923
ISI Accession Number ID
WOS:000293756800032
Funding AgencyGrant Number
University of Hong Kong
Research Grant Council of Hong Kong SAR, P. R. ChinaGRF HKU 7017/09P
HKU1/CRF/08
France/Hong Kong PROCORE-RGCF-HK30/07T
Funding Information:

This work was supported by the University of Hong Kong URC Seed Funding 2007, the Research Grant Council of Hong Kong SAR, P. R. China (GRF HKU 7017/09P, HKU1/CRF/08), and the France/Hong Kong PROCORE-RGC Joint Research Scheme 2008-2009 (F-HK30/07T).

References
References in Scopus
Grants
Reactive Metal-Ligand Multiple Bonded Complexes. From Biomimetic Reactions to Highly Efficient Chemical Synthesis
Development of anionic cascade reactions and other novel reactions of conjugated, accetylenic and allenic esters and thioesters. Toward the synthesis of biologically active compounds

 

DC FieldValueLanguage
dc.contributor.authorLi, Nen_HK
dc.contributor.authorOu, Jen_HK
dc.contributor.authorMiesch, Men_HK
dc.contributor.authorChiu, Pen_HK
dc.date.accessioned2011-07-27T01:33:57Z-
dc.date.available2011-07-27T01:33:57Z-
dc.date.issued2011en_HK
dc.identifier.citationOrganic And Biomolecular Chemistry, 2011, v. 9 n. 17, p. 6143-6147en_HK
dc.identifier.issn1477-0520en_HK
dc.identifier.urihttp://hdl.handle.net/10722/135349-
dc.description.abstractA conjugate reduction of α,β-unsaturated thioesters catalyzed by copper hydride using PMHS as stoichiometric reductant has been developed. 1,2-Bis(diphenylphosphino)benzene (BDP) was the most effective ligand for this reduction. Saturated thioesters could be produced in excellent yields when the substituent on the thiol is not sterically-demanding. This protocol was applied to induce the reductive aldol cyclization of keto-enethioates, which could offer β-hydroxythioesters in moderate to good yields. © 2011 The Royal Society of Chemistry.en_HK
dc.languageengen_US
dc.publisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/obcen_HK
dc.relation.ispartofOrganic and Biomolecular Chemistryen_HK
dc.titleConjugate reduction and reductive aldol cyclization of α,β- unsaturated thioesters catalyzed by (BDP)CuHen_HK
dc.typeArticleen_HK
dc.identifier.emailChiu, P:pchiu@hku.hken_HK
dc.identifier.authorityChiu, P=rp00680en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1039/c1ob05352cen_HK
dc.identifier.pmid21773644-
dc.identifier.scopuseid_2-s2.0-80052041200en_HK
dc.identifier.hkuros186267en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-80052041200&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume9en_HK
dc.identifier.issue17en_HK
dc.identifier.spage6143en_HK
dc.identifier.epage6147en_HK
dc.identifier.isiWOS:000293756800032-
dc.publisher.placeUnited Kingdomen_HK
dc.relation.projectReactive Metal-Ligand Multiple Bonded Complexes. From Biomimetic Reactions to Highly Efficient Chemical Synthesis-
dc.relation.projectDevelopment of anionic cascade reactions and other novel reactions of conjugated, accetylenic and allenic esters and thioesters. Toward the synthesis of biologically active compounds-
dc.identifier.scopusauthoridLi, N=49963785700en_HK
dc.identifier.scopusauthoridOu, J=35234687200en_HK
dc.identifier.scopusauthoridMiesch, M=7004636759en_HK
dc.identifier.scopusauthoridChiu, P=11140148700en_HK
dc.identifier.issnl1477-0520-

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