Enantioselective Annulation of α,β-Unsaturated N-Acyliminium Ions with β-Keto Ester Enolates via Cooperative Palladium and Brønsted Acid Catalysis.
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DOI: 10.1021/acs.orglett.2c01265
Abstract: We herein report a cooperative palladium- and Brønsted acid-catalyzed strategy toward the first enantioselective annulation of in situ generated α,β-unsaturated N-acyliminium ions with chiral metal enolates. Novel polycyclic oxoisoindoles featuring three contiguous stereogenic centers have… read more here.
Keywords: unsaturated acyliminium; palladium nsted; nsted acid; acyliminium ions ... See more keywords
Trapping of N-Acyliminium Ions with Enamides: An Approach to Medium-Sized Diaza-Heterocycles.
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DOI: 10.1021/acs.orglett.8b01407
Abstract: Enamides equipped with N-acyliminium ion precursors were obtained through reduction of ynamides tethered to N-imides. Intramolecular TMSOTf-mediated trapping of N-acyliminium ions provided a variety of polyfunctionalized medium-sized diaza-heterocycles of putative pharmacological interest. read more here.
Keywords: sized diaza; diaza heterocycles; medium sized; acyliminium ions ... See more keywords
Stereoselective nucleophilic addition reactions to cyclic N-acyliminium ions using the indirect cation pool method: Elucidation of stereoselectivity by spectroscopic conformational analysis and DFT calculations
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DOI: 10.3762/bjoc.14.100
Abstract: In this study, six-membered N-acyliminium ions were generated by the “indirect cation pool” method and reacted with several nucleophiles. These reactions afforded disubstituted piperidine derivatives with high diastereoselectivities and good to excellent yields. The conformations… read more here.
Keywords: indirect cation; cation pool; acyliminium ions; dft calculations ... See more keywords