ArticleThe Journal of organic chemistry2013
Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence.
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides.Angewandte Chemie (International ed. in English) · 2016Article
- Divergent C-H Insertion-Cyclization Cascades of N-Allyl Ynamides.Angewandte Chemie (International ed. in English) · 2015Article
- S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.Tetrahedron letters · 2015Article
- Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.The Journal of organic chemistry · 2014Article
- Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.Chemical communications (Cambridge, England) · 2014Article
- Ynamides in ring forming transformations.Accounts of chemical research · 2014Article
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Abstract
We describe here details of our investigations into Pd-catalyzed and thermal aza-Claisen-carbocyclizations of N-allyl ynamides to prepare a variety of α,β-unsaturated cyclopentenimines. The nature of the ynamide electron-withdrawing group and β-substituent plays critical roles in the success of this tandem cascade. With N-sulfonyl ynamides, the use of palladium catalysis is required, as facile 1,3-sulfonyl shifts dominate under thermal conditions. However, since no analogous 1,3-phosphoryl shift is operational, N-phosphoryl ynamides could be used to prepare similar cyclopentenimines under thermal conditions through zwitter ionic intermediates that undergo N-promoted H-shifts. Alternatively, by employing ynamides bearing tethered carbon nucleophiles, the zwitter ionic intermediates could be intercepted, giving rise rapidly to more complex fused bi- and tricyclic scaffolds.
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