FORMALDEHYDE SAMP-HYDRAZONE AS A NEUTRAL CHIRAL FORMYL ANION AND CYANIDE EQUIVALENT - ASYMMETRIC MICHAEL ADDITIONS TO NITROALKENES

Authors
ENDERS D SYRIG R RAABE G FERNANDEZ R GASCH C LASSALETTA JM LLERA JM
Citation
D. Enders et al., FORMALDEHYDE SAMP-HYDRAZONE AS A NEUTRAL CHIRAL FORMYL ANION AND CYANIDE EQUIVALENT - ASYMMETRIC MICHAEL ADDITIONS TO NITROALKENES, Synthesis, (1), 1996, pp. 48
Citations number
61
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
1
Year of publication
1996
Database
ISI
SICI code
0039-7881(1996):1<48:FSAANC>2.0.ZU;2-X
Abstract
The enantioselective synthesis of alpha-substituted beta-nitro nitrile s 4 and beta-nitroaldehydes 5 by Michael addition of formaldehyde SAMP -hydrazone 1 to nitroalkenes 2 in excellent overall yields and high en antiomeric excesses (ee = 90- > 99%) is described. Compound 1 constitu tes a neutral chiral formyl anion and cyanide equivalent. The absolute configuration was determined by X-ray structure analysis of the cryst alline SAMP-hydrazone 1,4-adduct 3e.