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Synfacts 2009(7): 0755-0755  
DOI: 10.1055/s-0029-1217291
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Role of Diethylaniline in the Reduction of 1,3-Dicarbonyl Compounds

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
R.-J. Chein, Y.-Y. Yeung, E. J. Corey*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

The authors reported that CBS ­reduction of 2,2-disubstituted cycloalkan-1,3-diones or hindered 2,2-disubstituted cyclic ketones using catecholborane as reductant proceeds with greater selectivity than when PhNEt2 is added. ­After careful experiments, it is believed that the beneficial effect of this additive may be due to the ability of this amine to catalyze the conversion of a minor harmful impurity in catalyst preparations to the active catalyst.