Simple Asymmetric Synthesis of 2<i>H</i>-Azirines Derived from Phosphine Oxides

Palacios, Francisco; Retana, Ana M. Ochoa de; Gil, and Jose Ignacio; Ezpeleta, Jose Marı́a

doi:10.1021/jo9915426

Cited by 84 publications

(46 citation statements)

References 31 publications

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“…Further, tuning the structure of the azirine by substituting a diphenylphosphoryl group for an ester group led to 22. [15] Treatment of 22 with 1a under the conditions described before yielded solely 25 in an acceptable yield. We inferred that the formation of unexpected 24 and 25 is the result of a synergistic influence of the acidic Scheme 5.…”

Section: Resultsmentioning

confidence: 90%

Stereoselective Addition of Sulfone Carbanions to C=N: A Critical Dependence on the Stability and Reactivity of the Amide Anions in MIRC Reactions

et al. 2004

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Section: Resultsmentioning

confidence: 90%

Stereoselective Addition of Sulfone Carbanions to C=N: A Critical Dependence on the Stability and Reactivity of the Amide Anions in MIRC Reactions

et al. 2004

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“…In 2000, an asymmetric Neber reaction was developed by Palacios et al for the preparation of constituants of naturally occurring antibiotics, such as alkyl-and aryl-substituted 2H-azirines bearing a phosphonate group in the 2-position of the ring [46]. As shown in Scheme 28, the Neber reaction of -phosphorylated tosyloximes 65 provided the corresponding 2H-azirines 66 in excellent yields along with low to good enantioselectivities of up to 82% ee when employing quinidine as organocatalyst.…”

Section: Asymmetric Azirination Through Neber Approachesmentioning

confidence: 99%

Applications of Chiral Three-membered Rings for Total Synthesis: A Review

Dalpozzo¹,

Lattanzi

Pellissier

2017

COC

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This review updates recent applications of asymmetric aziridination, azirination, thiirination, epoxidation, and cyclopropanation in the total synthesis of biologically active compounds, including natural products, using chiral substrates or chiral catalysts, covering the literature since 2000. The interest towards these synthetic methodologies of chiral three-membered rings has increased in the last decade, dictated either by the biological activities that display many naturally occurring products bearing a three-membered unit or by the ring strain of three-membered rings making them useful precursors of many more complex interesting molecules. Classic as well as modern protocols in asymmetric aziridinations, azirinations, epoxidations, thiirinations, and cyclopropanations have been widely applied as key steps of a number of syntheses of important products. Although the use of chiral substrates and auxiliaries is still highly employed particularly in asymmetric aziridination and cyclopropanation, the development of enantioselective catalytic methodologies has witnessed exponential growth during the last decade. The present review is subdivided into three parts, dealing successively with the use of chiral nitrogen-containing three-membered rings, chiral epoxides and thiiranes, and chiral cyclopropanes in total synthesis.

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“…Azirines have been shown to naturally occur in antibiotics [27][28][29][30], precursors for the synthesis of aziridines [14,[31][32][33], and, when derivatized with phosphorus substituents, shown to regulate many important biological functions [34]. N-Acylmethylbenzotriazoles [35,36] 13 with hydroxylamine hydrochloride provided oximes 14 as single isomers.…”

Section: Azirinesmentioning

confidence: 99%

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

Beagle

2015

Topics in Heterocyclic Chemistry

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Application of benzotriazole methodology for the preparation of nitrogen-containing heterocyclic compounds is summarized in this review. The characteristic advantages of benzotriazole are first briefly considered followed by an overview of its use in the synthesis of heterocycles organized by the ring size. Finally, the use of benzotriazole in the synthesis of bicyclic systems is showcased in only selected examples.

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Simple Asymmetric Synthesis of 2H-Azirines Derived from Phosphine Oxides

Cited by 84 publications

References 31 publications

Stereoselective Addition of Sulfone Carbanions to C=N: A Critical Dependence on the Stability and Reactivity of the Amide Anions in MIRC Reactions

Stereoselective Addition of Sulfone Carbanions to C=N: A Critical Dependence on the Stability and Reactivity of the Amide Anions in MIRC Reactions

Applications of Chiral Three-membered Rings for Total Synthesis: A Review

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

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