Direct Catalytic Aldol-Type Reactions Using RCH2CN
- 29 July 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (17) , 3147-3150
- https://doi.org/10.1021/ol035206u
Abstract
A copper fluoride-catalyzed cyanomethylation that can be applied to a wide range of ketones and aldehydes was developed using TMSCH2CN as a nucleophile. The reaction was extended to a conceptually more advanced copper alkoxide-catalyzed direct addition of alkylnitriles to aldehydes, which can act as a surrogate direct catalytic aldol reaction of esters. These reactions can be applied to the first catalytic enantioselective cyanomethylation of ketones and direct catalytic enantioselective cyanomethylation of aldehydes.Keywords
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