439584-65-3Relevant academic research and scientific papers
Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine
Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko
, p. 11047 - 11059 (2020/10/12)
The transamination of α-keto acids with 2-phenylglycine is an effective methodology for directly synthesizing unprotected α-amino acids. However, the synthesis of 2-arylglycines by transamination is problematic because the corresponding products, 2-arylglycines, transaminate the starting arylglyoxylic acids. Herein, we demonstrate the use of commercially available l-2-(2-chlorophenyl)glycine as the nitrogen source in the transamination of arylglyoxylic acids, producing the corresponding 2-arylglycines without interference from the undesired self-transamination process.
NaIO4/LiBr-mediated diastereoselective dihydroxylation of olefins: A catalytic approach to the prevost-woodward reaction
Emmanuvel, Lourdusamy,Ali Shaikh, Tanveer Mahammad,Sudalai, Arumugam
, p. 5071 - 5074 (2007/10/03)
(Chemical Equation Presented) LiBr catalyzes efficiently the dihydroxylation of alkenes to afford syn and anti diols with excellent diastereoselectivity depending upon the use of NaIO4 (30 mol %) or PhI(OAc)2 (1 equiv), respectively, as the oxidants. The oxidation of non-benzylic halides has been achieved for the first time to afford the corresponding diols in excellent yields.
New uses for the Burgess reagent in chemical synthesis: Methods for the facile and stereoselective formation of sulfamidates, glycosylamines, and sulfamides
Nicolaou,Snyder, Scott A.,Longbottom, Deborah A.,Nalbandian, Annie Z.,Huang, Xianhai
, p. 5581 - 5606 (2007/10/03)
Although the Burgess reagent (methoxycarbonylsulfamoyltriethylammonium hydroxide, inner salt) has found significant use in chemical synthesis as a dehydrating agent, almost no work has been directed towards its potential in other synthetic applications. As this article will detail, we have found that the Burgess reagent is remarkably effective at accomplishing a number of non-dehydrative synthetic tasks when applied to appropriate substrates, such as the formation of sulfamidates from 1,2-diols or epoxyalcohols, α- and β-glycosylamines from carbohydrates, and cyclic sulfamides from 1,2-aminoalcohols. Beyond delineating the power of these new reaction manifolds, we also describe the construction of a group of alternative Burgess-type reagents that extends the scope of these new reactions even further.
The use of pH to influence regio- and chemoselectivity in the asymmetric aminohydroxylation of styrenes
Nesterenko, Vitaliy,Byers, Joshua T.,Hergenrother, Paul J.
, p. 281 - 284 (2007/10/03)
(Matrix presented) The pH-controlled Sharpless asymmetric aminohydroxylation (AA) of styrenes provides 1-aryl-2-amino ethanols (regioisomer E enantio-, chemo-, and regioselectivity. As existing AA protocols typically give regioisomer A as the major reaction product when usin nitrogen sources, this method is a convenient alternative for the selective production of regioisomer B.
Bismuth(III)-catalyzed oxidative cleavage of aryl epoxides: substituent effects on the kinetics of the oxidation reaction
Boisselier, Veronique Le,Dunach, Elisabet,Postel, Michele
, p. 119 - 124 (2007/10/02)
Bismuth(III)mandelate catalyzes the oxidative C-C bond cleavage of a series of styrene epoxides in DMSO, to the corresponding aryl carboxylic acids.The reaction is accelerated in the presence of electron-donating groups substituting the phenyl ring.A good Hammet correlation of log kobs versus ? has been obtained, with a ρ of -1.08.Key words: Bismuth; Aryl epeoxide cleavage; Oxidation; Substituent effects; Bi(III) catalysis; Hammet correlation
