Please use this identifier to cite or link to this item: https://doi.org/10.1002/adsc.201000618
Title: Brønsted base-catalyzed tandem isomerization-Michael reactions of alkynes: Synthesis of oxacycles and azacycles
Authors: Liu, H.
Feng, W.
Kee, C.W.
Leow, D.
Loh, W.-T.
Tan, C.-H. 
Keywords: 2-alkylidenetetrahydrofurans
azacycles
Brønsted bases
oxacycles
tandem isomerization-Michael reaction
Issue Date: 17-Dec-2010
Citation: Liu, 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. https://doi.org/10.1002/adsc.201000618
Abstract: An 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.
Source Title: Advanced Synthesis and Catalysis
URI: http://scholarbank.nus.edu.sg/handle/10635/75684
ISSN: 16154150
DOI: 10.1002/adsc.201000618
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