Reductions of α,β-Unsaturated Ketones by NaBH4 or NaBH4 + CoCl2: Selectivity Control by Water or by Aqueous Micellar Solutions
2000; Wiley; Volume: 2000; Issue: 9 Linguagem: Inglês
10.1002/(sici)1099-0690(200005)2000
ISSN1434-193X
AutoresAndrea Aramini, Lucia Brinchi, Raimondo Germani, Gianfranco Savelli,
Tópico(s)Analytical Chemistry and Chromatography
ResumoOperationally 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.
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