Synthesis p. 48 - 52 (1996)
Update date:2022-07-29
Topics:
Enders, Dieter
Syrig, Ralf
Raabe, Gerhard
Fernández, Rosario
Gasch, Consolación
Lassaletta, José-María
Llera, José-Manuel
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.
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Doi:10.1021/ja01371a039
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(2002)
