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Reductions of α,β‐Unsaturated Ketones by NaBH 4 or NaBH 4 + CoCl 2 : Selectivity Control by Water or by Aqueous Micellar Solutions
Author(s) -
Aramini Andrea,
Brinchi Lucia,
Germani Raimondo,
Savelli Gianfranco
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200005)2000:9<1793::aid-ejoc1793>3.0.co;2-a
Subject(s) - chemistry , chemoselectivity , selectivity , aqueous solution , yield (engineering) , organic chemistry , isophorone , chalcone , green chemistry , reaction mechanism , catalysis , materials science , metallurgy
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 NaBH 4 or by the system NaBH 4 + CoCl 2 . 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.