Formaldehyde SAMP-Hydrazone as a Neutral Chiral Formyl Anion and Cyanide Equivalent: Asymmetric Michael Additions to Nitroalkenes
- 1 January 1996
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1996 (01) , 48-52
- https://doi.org/10.1055/s-1996-4174
Abstract
The enantioselective synthesis of α-substituted β-nitro nitriles 4 and β-nitroaldehydes 5 by Michael addition of formaldehyde SAMP-hydrazone 1 to nitroalkenes 2 in excellent overall yields and high enantiomeric excesses (ee=90->99%) is described. Compound 1 constitutes a neutral chiral formyl anion and cyanide equivalent. The absolute configuration was determined by X-ray structure analysis of the crystalline SAMP-hydrazone 1,4-adduct 3e.Keywords
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