Diastereoselective synthesis of multisubstituted isoindolines via Sequential Ugi and aza-Michael addition reaction

A new efficient and diastereoselective synthesis of multisubstituted isoindolines with two stereogenic centers via sequential Ugi/aza-Michael addition reaction was developed. Ugi-3CR of aldehydes 1, amines 2 and isocyanates 3 in the presence of catalytic amount of H3PO4 produced intermediates 4, whi...

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Bibliographic Details
Published in:Tetrahedron 2019-08, Vol.75 (33), p.4626-4631
Main Authors: Guan, Zhi-Rong, Wan, Qin, Ding, Ming-Wu
Format: Article
Language:English
Subjects:
Aza-Michael addition
Base catalyzed reaction
Isoindoline
Tetrazole
Ugi reaction
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Summary:A new efficient and diastereoselective synthesis of multisubstituted isoindolines with two stereogenic centers via sequential Ugi/aza-Michael addition reaction was developed. Ugi-3CR of aldehydes 1, amines 2 and isocyanates 3 in the presence of catalytic amount of H3PO4 produced intermediates 4, which were then transformed to isoindolines 5 with good 1,3-trans diastereoselectivity in the presence of K2CO3 by intramolecular aza-Michael addition. Sequential Ugi-azide and aza-Michael addition reaction of aldehydes 1, amines 2 and trimethylsilyl azide 6 also produced 4-tetrazolyl substituted isoindolines 8 with good 1,3-trans diastereoselectivity in the presence of potassium carbonate. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.07.006