138715-28-3Relevant articles and documents
Synthesis and Characterization of Chiral Oxazolidine-2-selones: A General One-Step Procedure from Readily Available Oxazolines
Peng, Jie,Barr, Mary E.,Ashburn, David A.,Odom, Jerome D.,Dunlap, R. Bruce,Silks, Louis A.
, p. 4977 - 4987 (2007/10/02)
The synthesis of a wide variety of chiral oxazolidine-2-selones from readily available 2-oxazolines has been accomplished in one step with yields ranging from 82 to 98percent.A mechanistic investigation of the formation of these selones has indicated the presence of intermediate anions which have been characterized by 13C and 77Se NMR spectroscopy.X-ray crystallographic data suggest the chiral selones exists as dimeric pairs or networks linked by unusual selenium hydrogen bonds.These chiral reagents exhibit extraordinary 77Se chemical shift sensitivity and are useful for the detection and quantitation of chirality at remotely disposed chiral centers.
Synthesis of (4S,5R)-(-)-4-Methyl-5-phenyloxazolidine-2-selone: A Chiral Auxiliary Reagent Capable of Detecting the Enantiomers of (R,S)-Lipoic Acid by 77Se Nuclear Magnetic Resonance Spectroscopy
Silks, Louis A.,Peng, Jie,Odom, Jerome D.,Dunlap, R. Bruce
, p. 2495 - 2498 (2007/10/02)
(4S,5R)-(-)-4-Methyl-5-phenyloxazolidine-2-selone was constructed in 5 steps on the 10-gram scale. 77Se NMR spectroscopic studies revealed that this selone served as a remarkably sensitive chiral auxiliary agent which readily distinguished the selone-coup