17016-83-0Relevant articles and documents
Bis(o-nitrophenyl) carbonate as a new reagent for the synthesis of chiral oxazolidin-2-ones
Simon, Monika,Micle, Andreea,Badea, Valentin,Csunderlik, Carol
, p. 2633 - 2639 (2009)
Bis(o-nitrophenyl) carbonate reacts under mild conditions with chirals 1,2-amino alcohols and, after addition of DMAP, affords the corresponding oxazolidin-2-ones in very good yields.
Single-Pot Reductive Conversion of Amino Acids to Their Respective 2-Oxazolidinones Employing Trichloromethyl Chloroformate as the Acylating Agent: A Multigram Synthesis
Pridgen, Lendon N.,Prol, J.,Alexander, Bruce,Gillyard, L.
, p. 3231 - 3233 (1989)
-
Chiral Dipole-Stabilized Anions: Experiment and Theory in Nonbenzylic Systems. 100percent Stereoselective Deprotonation and Two-Electron vs Single-Electron Transfer in the Chemistry of Lithium and Copper Piperidinooxazolines
Gawley, Robert E.,Hart, Georgina C.,Bartolotti, Libero J.
, p. 175 - 181 (1989)
A chiral oxazoline derived from valine mediates the 100percent stereoselective deprotonation of the 2-position of piperidine, forming a single diastereomer organolithium, which is dipole-stabilized.The organolithium species undergoes either two electron or single electron transfer processes, but the latter predominate for most electrophiles.The corresponding cuprates undergo only single electron transfer processes.MNDO calculations indicate little difference in energy between most of the conformational and stereoisomers of the organolithium, suggesting that the single organolithium diastereomer is formed under kinetic control.Mechanistic rationales for the unprecedented deprotonation, as well as the single electron transfer processes, are presented.
Synthesis of a diastereomer of the marine macrolide lytophilippine A
Klüppel, André,Gille, Annika,Karayel, Ceren Ester,Hiersemann, Martin
supporting information, p. 2421 - 2425 (2019/03/29)
The synthesis of a diastereomer of lytophilippine A required 22 longest linear steps using known building blocks. Cross-metathesis/asymmetric aldol addition and regioselective esterification/ring-closing metathesis served as efficient combi tools for scaffold construction. Detailed NMR investigations in different solvent (systems) provide evidence for a deep-seated configurational misassignment of the molecule named lytophilippine A.
Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3
Song, Hai-Xia,Han, Zhou-Zhou,Zhang, Cheng-Pan
supporting information, p. 10907 - 10912 (2019/08/02)
Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.
