Operationally simple and environmentally benign procedures have been developed to selectively reduce different α,β- unsaturated ketones, 4,4-dimethylcyclohex-2-ene-1-one (1), isophorone (2), benzylideneacetone (3), chalcone (4) by NaBH4 or by the system NaBH4 + CoCl2. Alternative reaction media to the extensively used MeOH have been explored and new procedures take advantage of the acceleration and chemoselectivity induced by water or by aqueous micellar solutions. It was possible to selectively and quantitatively afford pure products of 1,2 and of 1,4 reduction as well as the totally reduced compounds (yield and selectivity 90%) by simple changes in the experimental conditions.
Reduction of alfa, beta-Unsaturated Ketones by NaBH4 or NaBH4 + CoCl2: Selectivity Control by Water or by Aqueous Micellar Solutions
BRINCHI, Lucia;GERMANI, Raimondo;SAVELLI, Gianfranco
2000
Abstract
Operationally simple and environmentally benign procedures have been developed to selectively reduce different α,β- unsaturated ketones, 4,4-dimethylcyclohex-2-ene-1-one (1), isophorone (2), benzylideneacetone (3), chalcone (4) by NaBH4 or by the system NaBH4 + CoCl2. Alternative reaction media to the extensively used MeOH have been explored and new procedures take advantage of the acceleration and chemoselectivity induced by water or by aqueous micellar solutions. It was possible to selectively and quantitatively afford pure products of 1,2 and of 1,4 reduction as well as the totally reduced compounds (yield and selectivity 90%) by simple changes in the experimental conditions.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
