Asymmetric Construction of Quaternary Stereocenters by Direct Organocatalytic Amination of α-Substituted α-Cyanoacetates and β-Dicarbonyl Compounds
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- 12 June 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (26), 8120-8121
- https://doi.org/10.1021/ja047704j
Abstract
The first organocatalytic highly enantioselective reactions of substituted α-cyanoacetates and β-dicarbonyl compounds with azodicarboxylates are reported. In the presence of 0.1−5 mol % of a quinidine-derived alkaloid β-ICD, optically active quaternary hydrazine adducts are obtained in very high yields and with enantioselectivities up to >98% ee. A two-step procedure for the cleavage of the hydrazine N−N bond using SmI2 is also demonstrated.Keywords
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