NaNO2–Ceric ammonium nitrate mediated conversion of acrylic esters and Baylis–Hillman derived acrylic esters into corresponding β-nitro acrylic esters

Synthesis and Analysis of the Conformational Preferences of 5‐Aminomethyloxazolidine‐2,4‐dione Scaffolds: First Examples of β2‐ and β2, 2‐Homo‐Freidinger Lactam Analogues

“…[15] For this reason, we exploited the opportunity to utilize a-substituted-a-hydroxy-b 2, 2 -amino acids for the preparation of Amo-derivatives carrying an explicit proteinogenic side chain. [31] Reduction of the nitro group gave the (S)-or (R)-b 2, 2 -amino ester 7 a [32] or 7 b, and coupling with the other residues under MW irradiation and standard coupling agents gave the linear homochiral tetra-peptide 9 a or heterochiral 9 b, respectively. [15,29] As a prototype for a side chain substituted amino acid surrogate, we prepared the model nonracemic (S)-or (R)-a-methyl-isoSer from a keto ester and nitromethane, using an adaptation of the catalytic enantioselective Henry reaction reported by Jørgensen (Scheme 7).…”

A Diels–Alder route to angularly functionalized bicyclic structures

“…We first examined the cycloaddition-denitration sequence in the context of dienophile 11 7 (itself prepared in one step from 9 , as shown) and synergistic diene 10 (Scheme 2). 8 In the event, 10 and 11 did undergo cycloaddition to afford a 1:1 ( exo : endo ) mixture of the readily separable adducts 12 and 13 .…”

Nucleophilic addition to nitroacrylates: application towards the synthesis of 2,3-dehydroamino acids and 2,3-diamino acids

“…The 3-nitrocrotonate 1a was prepared by reaction of the corresponding acrylic ester with NaNO 2 -ceric ammonium nitrate (CAN) as reported. 9 The 3-nitropentenoate 1b and b-nitrocinnamic esters 1c-d were obtained by the nitroaldol (Henry) reaction between the appropriate nitroalkanes and ethyl glyoxalate as described. 10,11 The 3-nitroacrylates 1a-b were obtained as single E-isomers while b-nitrocinnamates 1c-d were prepared as mixtures of E and Z isomers.…”

“…Very recently, Buevich et al 10 reported that anitrocinnamic esters can be efficiently prepared by the addition of a nitro group to cinnamic esters utilizing NaNO 2 -ceric ammonium nitrate (NaNO 2 -CAN) method. 9 Using this methodology the anitrocinnamates 7a-c were prepared as a mixture of E and Z isomers.…”