Formaldehyde SAMP-Hydrazone as a neutral chiral formyl anion and cyanide equivalent: Asymmetric Michael additions to nitroalkenes

D Enders, R Syrig, G Raabe, R Fernández, C Gasch…

文献索引：Enders, Dieter; Syrig, Ralf; Raabe, Gerhard; Fernandez, Rosario; Gasch, Consolacion; Lassaletta, Jose-Maria; Llera, Jose-Manuel Synthesis, 1996 , # 1 p. 48 - 52

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被引用次数: 36

摘要

The enantioselective synthesis of Ot-Sl1l) StlU. 1'[€ Cl B-nitro nitriles 4 and B-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 ...