Diastereoselective Synthesis of Tetracyclic Tetrahydroquinoline Derivative Enabled by Multicomponent Reaction of Isocyanide, Allenoate, and 2-Aminochalcone

Abstract

We report here a multicomponent protocol to assemble several polycyclic dihydropyran-fused tetrahydroquinoline structures with excellent diastereoselectivity. This procedure employs simple feedstocks to accomplish a series of diverse structures, which is difficult to attain by traditional sequences.

[3+2] regioselective annulation reaction of 2-arylidene-1,3-indandiones towards synthesis of spirocyclopentenes: understanding the mechanism of γ-attackvs.α-attack using DFT studies

“…Nucleophilic phosphine-catalysed annulation of allenes has emerged as a powerful tool for the construction of diverse carbocycles and heterocycles. 1 Various electrophiles such as activated alkenes, 2 enones, 3 ketones, 4 imines, 5 oxo-dienes, 6 cyclic ketimines, 7 chromenones, 8 azomethine imines, 9 salicyl N -thiophosphinyl imines, 10 alkylidene malononitriles, 11 exocyclic enones, 12 aldehydes, 13 N -acyldiazenes, 14 naphthaquinones, 15 p -quinine methide, 16 amino esters, 17 and diones 18 have been used for the annulation reaction. The first [3+2] asymmetric process was reported by Zhang et al 19 Later on several chiral annulation reactions were investigated.…”