Use of Achiral (Diphosphine)RuCl2(Diamine) Precatalysts as a Practical Alternative to Sodium Borohydride for Ketone Reduction

Stoichiometric sodium borohydride is frequently used in the chemoselective reduction of ketones to racemic secondary alcohols. Catalytic homogeneous hydrogenation using (diphosphine)RuCl2(diamine) complexes provides a practical and economic alternative. A range of substrates were investigated and th...

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Bibliographic Details
Published inOrganic process research & development Vol. 10; no. 5; pp. 1054 - 1058
Main Authors de Koning, Pieter D, Jackson, Mark, Lennon, Ian C
Format Journal Article
LanguageEnglish
Published American Chemical Society 15.09.2006
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Summary:Stoichiometric sodium borohydride is frequently used in the chemoselective reduction of ketones to racemic secondary alcohols. Catalytic homogeneous hydrogenation using (diphosphine)RuCl2(diamine) complexes provides a practical and economic alternative. A range of substrates were investigated and the optimum precatalyst identified in each case. Norcamphor was reduced with high diastereoselectivity using (Ph3P)2RuCl2(en); (E)-4-phenylbut-3-en-2-one was reduced with good chemoselectivity, and acetophenone was hydrogenated very efficiently using the same precatalyst. Isophorone and 3-dimethylaminopropiophenone were effectively hydrogenated using (dppf)RuCl2(en).
ISSN:1083-6160
1520-586X
DOI:10.1021/op060063n