63160-15-6Relevant academic research and scientific papers
Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines
Smith, Siobhan R.,Fallan, Charlene,Taylor, James E.,McLennan, Ross,Daniels, David S. B.,Morrill, Louis C.,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information, p. 10530 - 10536 (2015/07/07)
A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high d.r., yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.
N-Nosyl oxaziridines as terminal oxidants in copper(II)-catalyzed olefin oxyaminations
Deporter, Sandra M.,Jacobsen, Ashley C.,Partridge, Katherine M.,Williamson, Kevin S.,Yoon, Tehshik P.
scheme or table, p. 5223 - 5225 (2010/11/03)
We report that N-4-nosyl-3-phenyloxaziridine is an effective terminal oxidant for copper(II)-catalyzed oxyamination recently developed in our labs. This oxaziridine can be prepared on multi-gram scale and is easily purified by recrystallization. The products of oxyamination using this oxaziridine bear protecting groups that can be readily removed in high yields under mild conditions.
Cycloadditions of N-sulfonyl nitrones generated by Lewis acid catalyzed rearrangement of oxaziridines
Partridge, Katherine M.,Anzovino, Mary E.,Yoon, Tehshik P.
, p. 2920 - 2921 (2008/10/09)
We have developed cycloaddition reactions of novel, electron-deficient N-nosyl nitrones that arise from the titanium(IV)-catalyzed rearrangement of the corresponding N-nosyl oxaziridines. A diverse range of styrenes and oxaziridines react smoothly in this
A new general method for the preparation of N-sulfonyloxaziridines
Garcia Ruano, Jose Luis,Aleman, Jose,Fajardo, Cristina,Parra, Alejandro
, p. 5493 - 5496 (2007/10/03)
(Chemical Equation Presented) A simple procedure to obtain N-alkylsulfonyl- and N-arylsulfonyloxaziridines from the corresponding N-sulfinylimines involving a one-pot, two-step oxidation process with m-CPBA (1 equiv) and m-CPBA/KOH (1.1 equiv) is reported
Chemistry of Oxaziridines. 1. Synthesis and Structure of 2-Arenesulfonyl-3-aryloxaziridines. A New Class of Oxaziridines
Davis, Franklin A.,Lamendola, Joseph,Nadir, Upender,Kluger, Edward W.,Sedergran, Thomas C.,et al.
, p. 2000 - 2005 (2007/10/02)
A new class of oxaziridine derivatives, 2-arenesulfonyl-3-aryloxaziridines (2), is prepared by m-CPBA oxidation of sulfonimines (RSO2N=CHAr).These compounds are the first stable examples of this ring system to have a substituent other than carbon attached to nitrogen and are characterized by a highly electrophilic oxaziridine oxygen atom.These oxaziridines have the E configuration as determined by X-ray crystallography.The presence of the powerful electron-attracting sulfonyl group attached to nitrogen apparently has little effect on the structure of the oxaziridine three-membered ring.Of more significance are the observations that the nitrogen lone pair in 2 is opposite to one of the sulfonyl oxygens and that the long S-N bond length implies little if any conjugative interaction between sulfur and nitrogen.Attempts to prepare oxaziridines via oxidation of sulfonimines, 5, derived from acetophenone gave imidoyl ether 14, a novel Baeyer-Villiger oxidation product of a C-N double bond.
