Garcia-Urricelqui, Ane; de Cozar, Abel; Campano, Teresa E.; Mielgo, Antonia; Palomo, Claudio published the artcile< syn-Selective Michael Reaction of α-Branched Aryl Acetaldehydes with Nitroolefins Promoted by Squaric Amino Acid Derived Bifunctional Broensted Bases>, Safety of (9Z,12Z)-Methyl octadeca-9,12-dienoate, the main research area is stereoselective Michael aryl acetaldehyde nitroolefin bifunctional cinchona squaric peptide.
Here we describe a direct access to 2,2,3-trisubstituted syn γ-nitroaldehydes by addition of α-branched aryl acetaldehydes to nitroolefins promoted by a cinchona based squaric acid-derived amino acid peptide. Different α-Me arylacetaldehydes react with β-aromatic and β-alkyl nitroolefins to afford the Michael adducts in high enantioselectivity and syn-selectivity. NMR experiments and DFT calculations predict the reaction to occur through the intermediacy of E-enolate. The interaction between the substrates and the catalyst follows Papai’s model, wherein an intramol. H-bond interaction in the catalyst between the NH group of one of the tert-leucines and the squaramide oxygen seems to be key for discrimination of the corresponding reaction transition states. Thus, e.g., 2-phenylpropanal + (E)-4-chloro-β-nitrostyrene → I (84%, 95:5 dr, 94% ee).
European Journal of Organic Chemistry published new progress about Aldehydes Role: SPN (Synthetic Preparation), PREP (Preparation) (γ-nitro). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Safety of (9Z,12Z)-Methyl octadeca-9,12-dienoate.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics