132785-26-3Relevant academic research and scientific papers
Synthesis of Benzylic Alcohols by C-H Oxidation
Tanwar, Lalita,B?rgel, Jonas,Ritter, Tobias
supporting information, p. 17983 - 17988 (2019/11/14)
Selective methylene C-H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant. We attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. We envision that our method will be useful for applications in the discovery of drugs and agrochemicals.
Stereocontrolled synthesis of β-hydroxyphenylalanine and β- hydroxytyrosine derivatives
Easton,Hutton,Roselt,Tiekink
, p. 7327 - 7340 (2007/10/02)
Side-chain bromination of N-phthaloyl-(S)-phenylalanine and tyrosine derivatives, followed by treatment of the product bromides with silver nitrate in aqueous acetone, affords the corresponding (2S,3R)-β-hydroxy-α- amino acids, enantiospecifically and diastereoselectively. The diastereoselectivity depends on the carboxyl protecting group. tert-Butyl esters display greater stereoselectivity than the corresponding methyl esters, presumably as a result of a steric effect, while N-tert-butylamides react diastereospecifically due to a combination of steric and electronic effects.
SYNTHESIS OF HOMOCHIRAL HYDROXY-α-AMINO ACID DERIVATIVES
Easton, Christopher J.,Hutton, Craig A.,Tan, Eng Wui,Tiekink, Edward R. T.
, p. 7059 - 7062 (2007/10/02)
Treatment of N-phthaloyl-α-amino acid methyl esters with N-bromosuccinimide, followed by reaction with silver nitrate in aqueous acetone, affords homochiral hydroxy-α-amino acid derivatives, the stereochemistry of which is predetermined by that of the starting amino acids.
