ArticleOrganic letters2013
A highly stereoselective addition of lithiated ynamides to Ellman-Davis chiral N-tert-butanesulfinyl imines.
Article in Organic letters, 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.
- Asymmetric synthesis with ynamides: unique reaction control, chemical diversity and applications.Chemical Society reviews · 2020Article
- Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids.Angewandte Chemie (International ed. in English) · 2019Article
- 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
- S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.Tetrahedron letters · 2015Article
- Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.Chemical communications (Cambridge, England) · 2014Article
- Ynamides in ring forming transformations.Accounts of chemical research · 2014Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
A highly diastereoselective addition of lithiated ynamides to Ellman-Davis chiral imines is described. While additions of N-sulfonyl ynamides are highly stereoselective even without Lewis acids, the use of BF3-OEt2 completely reversed the stereoselectivity. In addition, oxazolidinone-substituted ynamides behaved differently and functioned better with BF3-OEt2, and the chirality of the oxazolidinone ring exerts no impact on the selectivity.
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