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

Author:
Guan, Zhi-Rong, Wan, Qin, Ding, Ming-Wu
Source:
Tetrahedron 2019 v.75 no.33 pp. 4626-4631
ISSN:
0040-4020
Subject:
aldehydes, amines, azides, catalytic activity, chemical reactions, chemical structure, diastereoselective synthesis, diastereoselectivity, phosphoric acid, potassium carbonate
Abstract:
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.
Agid:
6509371