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Please use this identifier to cite or link to this item: https://scholarbank.nus.edu.sg/handle/10635/93218
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dc.titleBrønsted base-catalyzed tandem isomerization-Michael reactions of alkynes: Synthesis of oxacycles and azacycles
dc.contributor.authorLiu, H.
dc.contributor.authorFeng, W.
dc.contributor.authorKee, C.W.
dc.contributor.authorLeow, D.
dc.contributor.authorLoh, W.-T.
dc.contributor.authorTan, C.-H.
dc.date.accessioned2014-10-16T08:21:46Z
dc.date.available2014-10-16T08:21:46Z
dc.date.issued2010-12-17
dc.identifier.citationLiu, H., Feng, W., Kee, C.W., Leow, D., Loh, W.-T., Tan, C.-H. (2010-12-17). Brønsted base-catalyzed tandem isomerization-Michael reactions of alkynes: Synthesis of oxacycles and azacycles. Advanced Synthesis and Catalysis 352 (18) : 3373-3379. ScholarBank@NUS Repository.
dc.identifier.issn16154150
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/93218
dc.description.abstractAn efficient synthesis of oxacycles and azacycles was developed using a Brønsted base-catalyzed tandem alkyne isomerization-Michael reaction sequence. Functionalized 2-alkylidenetetrahydrofurans were prepared by an intramolecular oxy-Michael reaction on an allene that was generated in situ from an alkynoate. The aza-Michael version using alkynylamines, alkynylamides and alkynyl carbamates led to piperidines, lactams and oxazolidinones, respectively. An enantioselective version of this reaction resulted in an axially chiral lactam with high enantioselectivity. Some alkynes, however, were unable to complete the intramolecular Michael reactions and provided enantioenriched allenes. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
dc.description.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1002/adsc.201000618
dc.sourceScopus
dc.subject2-alkylidenetetrahydrofurans
dc.subjectazacycles
dc.subjectBrønsted bases
dc.subjectoxacycles
dc.subjecttandem isomerization-Michael reaction
dc.typeArticle
dc.contributor.departmentCHEMISTRY
dc.description.sourcetitleAdvanced Synthesis and Catalysis
dc.description.volume352
dc.description.issue18
dc.description.page3373-3379
dc.description.codenJPCHF
dc.identifier.isiut000285397800039
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