457602-62-9Relevant academic research and scientific papers
Isolation and syn elimination of a peterson adduct to obtain optically pure product in the diastereoselective synthesis of oxazolidinone-functionalized enecarbamates
Solomon, Marissa R.,Saito, Hideaki,Sivaguru,Jockusch, Steffen,Inoue, Yoshihisa,Adam, Waldemar,Turro, Nicholas J.
body text, p. 362 - 366 (2010/04/23)
The Peterson reaction of (4R)-N-(trimethylsilyl)methyl-4-alkyloxazolidin-2- one gives (E/Z)-(4R)-N-(2', 3'- diphenylbut-1'-enyl)-4-alkyloxazolidin-2-ones (enecarbamates) with increasing (Z)-selectivity and moderate-to-high diastereoselectivity in the indi
Enecarbamates as Selective Substrates in Oxidations: Chiral-Auxiliary-Controlled Mode Selectivity and Diastereoselectivity in the [2+2] Cycloaddition and Ene Reaction of Singlet Oxygen and in the Epoxidation by DMD and mCPBA
Adam, Waldemar,Bosio, Sara G.,Turro, Nicholas J.,Wolff, Barbara T.
, p. 1704 - 1715 (2007/10/03)
The stereochemical course of the oxidation of chiral oxazolidinone-substituted enecarbamates has been studied for singlet oxygen (1O2), dimethyldioxirane (DMD), and m-chloroperbenzoic acid (mCPBA) by examining of the special structural and stereoelectronic features of the enecarbamates. Valuable mechanistic insight into these selective oxidations is gained. Whereas the R1 substituent on the chiral auxiliary is responsible for the steric shielding of the double bond and determines the sense of the π-facial diastereoselectivity, structural characteristic such as the Z/E configuration and the nature of the R 2 group on the double bond are responsible for the extent of the diastereoselectivity. Stereoelectronic steering by the vinylic nitrogen functionality controls the mode selectivity (ene reaction vs [2+2] cycloaddition) in the case of 1O2.
