124266-92-8Relevant academic research and scientific papers
Stereoselective Epoxidation of Allylic Carbamates with m-Chloroperbenzoic Acid: The Role of Cooperative Coordination
Jenmalm, Annika,Berts, Wei,Luthman, Kristina,Csoeregh, Ingeborg,Hacksell, Uli
, p. 1026 - 1032 (1995)
Stereoselective epoxidations of a series of allylic carbamate methyl esters 1a-d, homoallylic alcohols 1e-h, and acetates 1i-l have been performed using m-chloroperbenzoic acid (m-CPBA) as epoxidizing agent.Throughout, the formation of the threo epoxides was favored.This selectivity is probably due to a directing effect of the carbamate group which forms a hydrogen bond to the peracid.However, the threo/erythro isomeric ratio is also dependent on steric interactions and on the possibility of cooperative coordination of the peracid to other suitably positioned functionalities such as allylic methyl ester, homoallylic alcohol, and acetate groups.The results of the present study indicate that the methyl ester is a weaker directing group than the carbamate.However, the directing effect of the methyl ester is stronger than that of the homoallylic alcohol and acetate groups.A thermodynamic study of the epoxidation of two epimeric carbamate esters giving considerably different isomeric product ratios (9:1 compared to 2:1) indicates that the order in the transition state structure influences the isomeric ratios.
Peracid dependent stereoselectivity and functional group contribution to the stereocontrol of epoxidation of (E)-alkene dipeptide isosteres
Wiktelius, Daniel,Berts, Wei,Jensen, Annika Jenmalm,Gullbo, Joachim,Saitton, Stina,Cs?regh, Ingeborg,Luthman, Kristina
, p. 3600 - 3609 (2007/10/03)
Twelve Boc-protected phenylalanyl-phenylalanine and phenylalanyl-glycine trans-vinyl isosteres were epoxidised with magnesium monoperoxyphtalate hexahydrate (MMPP) and trifluoroperacetic acid, and the results have been compared with those from earlier stu
Stereoselective Epoxidation of Phe-Gly and Phe-Phe Vinyl Isosteres
Jenmalm, Annika,Berts, Wei,Li, Yi-Lin,Luthman, Kristina,Csoeregh, Ingeborg,Hacksell, Uli
, p. 1139 - 1148 (2007/10/02)
Novel Phe-Gly and Phe-Phe isosteres have been synthesized.Vinylic isosteres of Phe-Gly and Phe-Phe were prepared by facile Julia reactions, and the resulting stereoisomers were isolated and epoxidized (m-chloroperbenzoic acid).Observed stereoselectivities
Novel L-Phe-Gly mimetics
Li, Yi-Lin
, p. 4487 - 4490 (2007/10/02)
The syntheses of some novel dipeptidomimetics of potential biological interest are described. The reactions started from the vinyl isostere of Phe-Gly and were performed in high yields. Stereochemically pure products were isolated.
Renin inhibitors containing isosteric replacements of the amide bond connecting the P3 and P2 sites
Kaltenbronn,Hudspeth,Lunney,Michniewicz,Nicolaides,Repine,Roark,Stier,Tinney,Woo,Essenburg
, p. 838 - 845 (2007/10/02)
Renin inhibitors having 13 different isosteres connecting the P3 and P2 positions have been prepared. Synthetic routes and in vitro activity exhibited by these compounds are discussed. The two most potent compounds, 47 and 48, contai
