4.2 Article

CATALYTIC AND DIASTEREOSELECTIVE CASCADE REACTION FOR THE PREPARATION OF cis-1,3-DISUBSTITUTED ISOINDOLINE-AMINAL HYBRID COMPOUNDS

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HETEROCYCLES
卷 102, 期 4, 页码 723-730

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-21-14404

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A convenient and catalytic method for the diastereoselective construction of cis-1,3-disubstituted isoindoline skeletons has been developed, achieving complete diastereocontrol in the synthesis of a series of cis-1,3-disubstituted isoindoline-aminal hybrid compounds through direct aminalization of N-protected imines with a Michael acceptor and subsequent intramolecular aza-Michael reaction.
A convenient and catalytic method for the diastereoselective construction of cis-1,3-disubstituted isoindoline skeletons is described. In the presence of 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene as a base catalyst and under mild conditions, the direct aminalization of N-protected imines bearing a Michael acceptor using the aniline derivatives and the subsequent intramolecular aza-Michael reaction proceeded successfully in a short reaction time. A series of cis-1,3-disubstituted isoindoline-aminal hybrid compounds are obtained in moderate to good yield (44%-93%) with complete diastereocontrol.

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