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Abstract A convenient and efficient base-promoted cascade reaction for the synthesis of cis-1,3-disubstituted isoindolines has been reported herein. We discovered that various N-protected imines bearing a Michael acceptor react smoothly… Click to show full abstract
Abstract A convenient and efficient base-promoted cascade reaction for the synthesis of cis-1,3-disubstituted isoindolines has been reported herein. We discovered that various N-protected imines bearing a Michael acceptor react smoothly with several nitrogenous nucleophiles in the presence of 1,8-diazabicyclo[5.4.0]-7-undecene under mild conditions. cis-1,3-Disubstituted isoindolines bearing aminal functionality were assembled as a single diastereomer in moderate to good yields (52%–94%). This cascade process features the direct amidation of imines followed by the intramolecular aza-Michael reaction.
Journal Title: Tetrahedron Letters
Year Published: 2020
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