D. Enders, Dominik Förster, G. Raabe
Dec 19, 2008
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0
Influential Citations
6
Citations
Journal
The Journal of organic chemistry
Abstract
Alpha-amino nitriles, easily prepared from aldehydes, KCN, and an enantiopure secondary amine auxiliary, are metalated and used as nucleophiles in asymmetric Michael additions to nitroalkenes to afford the Michael adducts in good yields and good to excellent diastereoselectivities. After chromatographic purification, the diastereomerically pure 1,4-adducts are cleaved under acidic conditions to give the beta-nitro ketones in good yields and with two exceptions in good to excellent enantiomeric excesses (ee = 86-99%). The absolute configuration was determined by X-ray structure analysis.