Catalytic diastereoselective sulfimidation of diaryl sulfides and application of chiral sulfimides to asymmetric allylic alkylation

Takada, Hiroya; Oda, Masahiko; Oyamada, Arihiro; Ohe, Kouichi; Uemura, Sakae

doi:10.1002/(sici)1520-636x(2000)12:5/6<299::aid-chir2>3.0.co;2-s

Cited by 36 publications

(15 citation statements)

References 57 publications

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“…in moderate yield. Note that compared to the analogous reaction with chloramine-T as imidating agent (Scheme 3), 9 the d.e. obtained here was slightly lower.…”

Section: 21mentioning

confidence: 99%

Sulfur imidations: access to sulfimides and sulfoximines

2015

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Being mono-aza analogues of sulfoxides and sulfones, sulfimides and sulfoximines, respectively, are important compounds in asymmetric synthesis, crop protection and medicinal chemistry. For their preparation various methods have been developed. In the search for the optimal synthetic approach for a given target compound, several parameters have to be considered which also include safety issues and availability of starting materials. In this tutorial review, we present an overview of sulfur imidation methods, classified by imidating agents and compounds with a related behaviour. The aim of this survey is to provide a practical ''tool box'' for the synthetic chemist by mapping the advantages and disadvantages associated with the use of these compounds. Key learning points(1) Most imidating agents consist of the nitrogen atom to be transferred linked to a core fragment and a leaving group. (2) Sulfur imidation involves either the reaction between an electrophilic sulfonium salt and a nucleophilic nitrogen, or the addition of an electrophilic nitren(oid) species to a nucleophilic sulfur. (3) Toxicity and safety issues should be considered before choosing an imidation procedure. (4) Use of a catalytic amount of transition metal can considerably improve the imidation efficiency and allows stereoselective syntheses of sulfimides and sulfoximines.

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“…in moderate yield. Note that compared to the analogous reaction with chloramine-T as imidating agent (Scheme 3), 9 the d.e. obtained here was slightly lower.…”

Section: 21mentioning

confidence: 99%

Sulfur imidations: access to sulfimides and sulfoximines

2015

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“…Although sulfimides can be easily synthesized by various means,1, 5 their preparation in enantioenriched form is still challenging. The most prominent strategies involve the use of chiral auxiliaries3a, 6 or reagents 7. All of those, however, require stoichiometric amounts of chiral compounds that are usually prepared by multi‐step syntheses.…”

Section: Optimization Of Reaction Conditions[a]mentioning

confidence: 99%

Enantioselective Nitrene Transfer to Sulfides Catalyzed by a Chiral Iron Complex

2013

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“…[1][2][3] Chiral sul limines have also been developed as ligands for enantioselective transition-metal catalysis. 4,5 Recently, the biological signi cance of sul limines has drawn much attention. In 2009, Hudson and coworkers revealed that hydroxylysine-211 and methionine-93 in collagen IV was covalently cross-linked by a sul limine bond, which represents the rst sul limine group identi ed in biomolecules.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Sulfilimines Enabled by Copper-Catalyzed S-Arylation of Sulfenamides

Liang

Wells

Han

et al. 2021

Preprint

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Herein, an unprecedented synthetic route to sulfilimines via a copper-catalyzed Chan-Lam-type coupling of sulfenamides is presented. A key to success in this novel transformation is the chemoselective S-arylation of S(II) sulfenamides to form the S(IV) sulfilimines, overriding the competitive C-N bond formation that does not require a change in sulfur oxidation state. The mild and environmentally benign catalytic conditions enable broad functional group compability. A variety of diaryl or alkyl aryl sulfilimines could be efficiently prepared. The Chan-Lam coupling procedure could also tolerate alkenylboronic acids as coupling partners to afford alkenyl aryl sulfilimines, a class of scaffolds which cannot be directly synthesized via conventional imination strategies. The benzoyl protecting groups could be conveniently removed from the product which, in turn, could be readily transformed to several S(IV) and S(IV) derivatives.

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Catalytic diastereoselective sulfimidation of diaryl sulfides and application of chiral sulfimides to asymmetric allylic alkylation

Cited by 36 publications

References 57 publications

Sulfur imidations: access to sulfimides and sulfoximines

Sulfur imidations: access to sulfimides and sulfoximines

Enantioselective Nitrene Transfer to Sulfides Catalyzed by a Chiral Iron Complex

Synthesis of Sulfilimines Enabled by Copper-Catalyzed S-Arylation of Sulfenamides

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