49620-56-6Relevant academic research and scientific papers
Iron-catalyzed imidative kinetic resolution of racemic sulfoxides
Wang, Jun,Frings, Marcus,Bolm, Carsten
supporting information, p. 966 - 969 (2014/02/14)
Kinetic resolution of racemic sulfoxides requires either custom substrates or shows moderate enantioselectivity, leading to achiral coproducts (such as sulfones) as an intrinsic part of the process. A new strategy is demonstrated that allows the resolution of racemic sulfoxides through catalytic asymmetric nitrene-transfer reactions. This approach gives rise to both optically active sulfoxides and highly enantioenriched sulfoximines. By using a chiral iron catalyst and a readily available iodinane reagent, high selectivity factors have been achieved under very practical reaction conditions. With respect to the substrate scope, it is noteworthy that this unprecedented imidative kinetic resolution of racemic sulfoxides provides access to both aryl-alkyl and dialkyl sulfoximines in highly enantioenriched forms. Copyright
Enantioselective nitrene transfer to sulfides catalyzed by a chiral iron complex
Wang, Jun,Frings, Marcus,Bolm, Carsten
supporting information, p. 8661 - 8665 (2013/09/12)
Iron works: Enantioselective nitrene transfer to sulfide was accomplished by a chiral iron(III)/PyBOX catalyst (see scheme). Various sulfimides were thus obtained in high enantioselectivities and yields. Applications of this protocol to the syntheses of enantioenriched sulfoximines and an epoxide were also demonstrated. Copyright
Transannular, decarboxylative Claisen rearrangement reactions for the synthesis of sulfur-substituted vinylcyclopropanes
Craig, Donald,Gore, Sophie J.,Lansdell, Mark I.,Lewis, Simon E.,Mayweg, Alexander V. W.,White, Andrew J. P.
supporting information; experimental part, p. 4991 - 4993 (2010/08/22)
Unsaturated ε-lactones bearing an α-arylsulfonyl or α-arylsulfoximinyl substituent undergo stereoselective transannular, decarboxylative Claisen rearrangement to give substituted vinylcyclopropanes.
Asymmetric intramolecular Diels-Alder reactions of sulfoximine-activated trienes
Craig, Donald,Geach, Neil J.,Pearson, Christopher J.,Slawin, Alexandra M. Z.,White, Andrew J. P.,Williams, David J.
, p. 6071 - 6098 (2007/10/02)
A series of N-substituted sulfoximidoyl-1,6,8-nonatrienes and 1,7,9-decatrienes were synthesized and subjected to thermal intramolecular Diels-Alder (IMDA) reactions to give diastereomeric mixtures of substituted bicyclo[4.3.0]nonanes and -[4.4.0]decanes. The reactions showed varying selectivities. Endo/exo selectivity was interpreted in terms of a combination of steric factors and the asynchronous nature of the cycloadditions. Diastereofacial selectivity could be rationalised by considering attack by the diene on the less hindered face of the conformationally extended vinylic sulfoximine dienophile.
Chiral Recognition during the Reaction of Dienyliron Complexes with Sulphoximine-stabilized Enolates
Pearson, Anthony J.,Yoon, Jaeyon
, p. 1467 - 1469 (2007/10/02)
The first example is reported of chiral recognition during enolate nucleophile addition to dienyliron complexes; enantiomeric excesses of up to 50percent were obtained by reaction of complex (1) with enolates derived from the sulphoximinyl ester derivativ
