Lewis acid mediated multisegment coupling cascade is designed for the synthesis of densely substituted 4-alkoxy quinolines via an oxonium ion triggered alkyne carboamination sequence involving C-C and C-N bond formations. Cyclic ether fused-quinolines could also be accessed using this fast, operationally simple, high yielding, chemoselective and functional group tolerant method. Versatility and utility of this methodology is demonstrated by postfunctionalization of products obtained and its use in synthesis of potent drug molecules.
Ac hiral aluminum catalyst systemh as been developed for the enantioselective vinylation of aldehydes. b,b-Disubstituted (E)-vinylaluminum reagents,g eneratedr egio-and stereoselectively by the carboalumination of terminal alkynes with trimethylalumunim (Me 3 Al),w ere useds traightforwardly without transmetalation to vinyltitanium reagents in the subsequent enantioselective addition to aldehydes with aD PP-H 8 -BINOL-derivedc hiral aluminum catalyst at low catalyst loading (5 mol%). Ther eactiona ffordedt he corresponding enantiomerically enriched secondary allylic alcohols with ar eversalo ft he selectivity observed in closely related reactions catalyzed by ac hiral titanium complex derived from the same ligand.
A novel strategy of initiating an organocatalysed dynamic kinetic resolution (dr up to 99 : 1 and er up to 94 : 6) for the synthesis of chiral trans-2,5-dialkylcyclohexanones by an asymmetric conjugate addition of dimethyl malonate on to 6-substituted cyclohexenones is reported.
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