Recent Advances in the Catalytic Asymmetric Reactions of Oxaziridines

Ren, Qiao; Yang, Wen; Lan, Yunfei; Qin, Xurong; He, Youzhou; Yuan, Lujiang

doi:10.3390/molecules23102656

Cited by 16 publications

(9 citation statements)

References 102 publications

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“…Besides α‐halogenations of β‐ketoesters, we also became interested in investigating analogous α‐hydroxylations. We first tested the use of oxaziridines 27 as electrophilic O‐transfer agents (Scheme 11A) [25a,39] . Hereby we found that the use of catalyst VII‐5 allows for the synthesis of products 28 with very high enantioselectivities under base‐free conditions.…”

Section: Selected Applicationsmentioning

confidence: 99%

(Thio)urea Containing Chiral Ammonium Salt Catalysts

Waser

Winter

Mairhofer

2022

The Chemical Record

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Dedicated to Prof. Alois Fürstner on the occasion of his 60 th birthday (thanks for giving me a chance to join your group, thanks for everything I learned from you, and thanks for all your support over all the years lieber Alois!!).Abstract: (Thio)-urea-containing bifunctional quaternary ammonium salts emerged as powerful non-covalently interacting organocatalysts over the course of the last decade. The most commonly employed catalysts in this field are either based on Cinchona alkaloids, α-amino acids, or trans-cyclohexane-1,2-diamine. Our group has been heavily engaged in the design and use of such catalysts, i. e. trans-cyclohexane-1,2-diamine-based ones for around 10 years now, and it is therefore the intention of this short personal account to provide an overview of the, at least in our opinion, most significant and pioneering achievements in this field by looking on catalyst design and asymmetric method development, with a special focus on our own contributions.

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Section: Selected Applicationsmentioning

confidence: 99%

(Thio)urea Containing Chiral Ammonium Salt Catalysts

Waser

Winter

Mairhofer

2022

The Chemical Record

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“…The asymmetric α‐hydroxylations of carbonyl compounds could be considered as most widely employed applications of N ‐sulfonyl oxaziridienes [1c,d,f] . The α‐hydroxy carbonyl moiety was a common building block found in many biologically active materials, such as pheromones, sugars, antibiotics, terpenes and alkaloids (Figure 4).…”

Section: Reactivities Of Oxaziridinesmentioning

confidence: 99%

“…The applications of N ‐sulfonyl oxaziridines in organic synthesis were summarized by Davis in 2018 [1c] . In a parallel report, Yuan and co‐workers highlighted the oxaziridines mediated asymmetric reactions [1d] . Similarly, preparations and synthetic applications of diaziridines were reviewed by Makhova et al.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Preparations and Synthetic Applications of Oxaziridines and Diaziridines

et al. 2021

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Oxaziridines and diaziridines have been used as versatile intermediates due to their high ring strain as well as the reactive CÀ O/N bond, for the synthesis of diverse range of nitrogen containing compounds. In the past few decades, numerous novel and handy methodologies on the preparations and utilizations of both the oxaziridines and diaziridines have been developed. In spite of few published reviews in the area (almost a decade back), the synthetic communities have made tremendous progress in their preparations and utilizations. This review has demonstrated the comprehensive advancement in the chemistry of oxaziridines and diaziridines for the last few years (almost a decade). 2.4. Oxaziridines from Ketimines 3. Reactivities of Oxaziridines 3.1. Oxygen Atom Transfer Reactions 3.2. Nitrogen Atom Transfer Reactions 3.3. Rearrangement Reactions of Oxaziridines 3.4. Cycloaddition Reactions 4. Synthesis of Diaziridines 4.1. Diaziridines from Imine Substrates 4.2. Bi-Diaziridines and Monocyclic Diaziridines using Nosyloxycarbamate 4.3. Alkenyl Diaziridines 4.4. Diaziridines using HOSA Reagent 4.5. N-Cyclopropyl Diaziridines 4.6. Synthesis of Diaziridines via Photocatalysis 5. Reactivities of Diaziridines and its Derivatives 6. Diaziridines as Intermediates 7. Conclusions

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“…Despite the high selectivities that were obtained hereby, combined with an efficient kinetic resolution of the oxaziridines, we recently looked for strategies avoiding the need for the oxaziridine synthesis. Inspired by results by the Ooi group, who reported the catalytic asymmetric synthesis of enantioenriched oxaziridines from imines 4 via a Payne-type oxidation (Scheme D), − we thought about developing a process where oxaziridines 2 would be generated in situ starting from imines 4 and may then be utilized for the α-hydroxylation of 1 …”

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confidence: 99%

Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters

2020

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The synergistic use of chiral bifunctional ammonium iodide catalysts in combination with simple catalytically relevant aldimines allows for an unprecedented asymmetric α-hydroxylation reaction of β-ketoesters using H 2 O 2 . The reaction proceeds via in situ formation of a hypervalent iodine species, which then reacts with the used aldimine to generate an activated electrophilic oxygen transfer reagent.

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Recent Advances in the Catalytic Asymmetric Reactions of Oxaziridines

Cited by 16 publications

References 102 publications

(Thio)urea Containing Chiral Ammonium Salt Catalysts

(Thio)urea Containing Chiral Ammonium Salt Catalysts

Recent Advances in the Preparations and Synthetic Applications of Oxaziridines and Diaziridines

Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters

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