Synthesis of substituted piperidines by enantioselective desymmetrizing intramolecular aza-Michael reactions.
An organocatalytic enantioselective intramolecular aza-Michael reaction has been described for the first time in a desymmetrization process employing substrates different from cyclohexadienones. By using 9-amino-9-deoxy-epi-hydroquinine as the catalyst and trifluoroacetic acid as a co-catalyst, a series of enantiomerically enriched 2,5-and 2,6-disubstituted piperidines have been obtained in good yields and with moderate diastereoselectivity. Depending on the catalyst/co-catalyst loading ratio, either the major or the minor diastereoisomer of the final piperidine products was achieved with high levels of enantioselectivity. Finally, some mechanistic insights have been considered by means of …
Unexpected metal-free synthesis of trifluoromethyl arenes via tandem coupling of dicyanoalkenes and conjugated fluorinated sulfinyl imines
A novel strategy for the synthesis of policyclic trifluoromethyl arenes has been devised. It involves a DBU-promoted tandem cycloaromatization reaction of dicyanoalkenes and fluorinated conjugated sulfinyl imines. This unprecedented transformation is a metal-free and air-tolerant process that takes place from readily available starting materials under mild reaction conditions.
CCDC 1829500: Experimental Crystal Structure Determination
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CCDC 1989940: Experimental Crystal Structure Determination
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CCDC 1989936: Experimental Crystal Structure Determination
Related Article: Alvaro Sanz-Vidal, Daniel Gaviña, Lia Sotorríos, Enrique Gómez-Bengoa, Fernando López Ortiz, María Sánchez-Roselló, Carlos del Pozo|2021|Chem.Commun.|57|8023|doi:10.1039/D1CC03161A