Kinetic Diastereomer Differentiation in Au(III)- and Bi(III)-Catalyzed Benzylic Arylation: Concise and Stereocontrolled Synthesis of 2-Amino-1,1-diarylalkanes was written by Chenard, Etienne;Hanessian, Stephen. And the article was included in Organic Letters in 2014.Application In Synthesis of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate This article mentions the following:
2-Nitro- and 2-azido-1,1-diarylalkanes with electron-donating aryl groups such as I [R = 2,4-(MeO)2C6H3, 4-methoxy-1-naphthyl, 4-MeOC6H4, 2,3,4-(MeO)3C6H2, 5-methyl-2-furyl, 2,6-(MeO)2-4-(H2C:CH)C6H2; R1 = H, Me, Et, n-Pr, i-Pr, allyl, PhCH2; R2 = O2N, N3] were prepared diastereoselectively as their syn diastereomers in 14-91% yields (all but one > 50% yields) and in 5:1->20:1 diastereoselectivities by nucleophilic substitution of benzylic alcs. such as I (R = HO; R1 = H, Me, Et, n-Pr, i-Pr, allyl, PhCH2; R2 = O2N, N3) with arenes in the presence of either AuCl3 or Bi(OTf)3; an azidotosylamide I (R = TsNH; R1 = Et; R2 = O2N; Ts = 4-MeC6H4SO2) was prepared using TsNH2 as a nucleophile instead of an arene. Nonracemic benzyl alcs. were prepared from phenylalanine and incorporated into nonracemic diarylalkyl azides; variation of the aryl group in the nitroalkyl and azidoalkyl benzyl alcs. allowed access in some cases to both syn- and anti-diastereomers of diarylalkyl azido and nitro compounds Kinetic resolution occurred in reactions of diastereomeric mixtures of nitro alcs., with the syn diastereomers of the reactants converted more rapidly to the corresponding products than the anti-diastereomers; both diastereomeric alcs. yielded the syn product. The structure of I (R = 4-MeO-1-naphthyl; R1 = Et; R2 = O2N) was determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9Application In Synthesis of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate).
(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Application In Synthesis of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics