Lewis Acid-Catalyzed Synthesis of Aziridines

Casarrubios, Luis; Pérez, Julio; Brookhart, Maurice; Templeton, Joseph L.

doi:10.1021/jo961391w

Cited by 173 publications

(96 citation statements)

References 22 publications

(13 reference statements)

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“…Considerando que a reatividade de EDA frente a iminas é normalmente baixa, existe a necessidade de se empregar um catalisador de modo a conduzir adequadamente a formação de aziridinas. Diversos tipos de ácidos de Lewis [88][89][90][91][92][93] já foram descritos como catalisadores para essa reação, entre eles BF 3 , AlCl 3 , TiCl 4 , ZnI 2 , InCl 3 e triflatos como Zn(OTf) 2 , Yb(OTf) 3 e La(OTf) 3 , incluindo versões assimétricas 94 (Esquema 29). Ácidos de Bronsted, como ácido clorídrico, trifluoroacético ou trifluorometanossulfônico, também se mostraram eficientes 95 para este tipo de transformação.…”

Section: Aziridinas a Partir Da Inserção De Carbono Em Iminasunclassified

Recentes avanços na preparação de aziridinas. Aplicações sintéticas e implicações mecanísticas

Bisol¹,

Sá²

2007

Quím. Nova

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Recebido em 22/8/05; aceito em 3/2/06; publicado na web em 30/8/06RECENT ADVANCES IN THE PREPARATION OF AZIRIDINES AND THEIR APPLICATION IN ORGANIC SYNTHESIS. This article surveys a selection of the most recent advances in aziridine synthesis. Novel synthetic methods and new insights into existing methodologies for the selective construction of the title compounds reported in the past decade are discussed in terms of synthetic applicability and environmentally benign conditions. Mechanisms involving stereoselective preparation of structurally diverse aziridines are also presented in order to highlight the most important issues associated with the synthesis of these versatile building blocks.

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Section: Aziridinas a Partir Da Inserção De Carbono Em Iminasunclassified

Recentes avanços na preparação de aziridinas. Aplicações sintéticas e implicações mecanísticas

Bisol¹,

Sá²

2007

Quím. Nova

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“…Encouraged by the successful activation of imines by Lewis acids in allylation reactions [10] and aziridination of BF 3 ?OEt 2 activated imines with ethyl diazoacetate [20], we examined the BF 3 ?OEt 2 and TMSCl activation of imines in the ylide reaction for the preparation of vinyl-and ethynyl-aziridines [21] (Scheme 14). A variety of aromatic aldimines, either N-aryl or N-alkyl, could be aziridinated with good to excellent yields, but aziridination failed when aliphatic aldimines were used as substrates.…”

Section: Aziridination With Iminesmentioning

confidence: 99%

Stereoselective reactions with imines

Dai¹,

Yang²,

Hou³

et al. 1999

Pure and Applied Chemistry

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By the activation of general imines or using activated imines (N-tosylimines or Ndiphenyl-phosphinoylimines), we developed three types of stereoselective reactions with imines: aldol reaction, allylation, and aziridiantion, and optically active 2-imidazolines and aziridines were obtained. According to experimental evidences, Sakurai-Hosomi reactions in the presence of catalytic amount of TBAF was demonstrated to be a¯uoride-triggered autocatalytic mechanism. In addition, optically active 2,3-diamino acids were also synthesised conveniently by chemical transformations of 2-imidazolines.

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“…Encouraged by the successful activation of imines by Lewis acids in allylation reactions [19] and aziridination [20] of BF 3 ؒ OEt 2 activated imines with ethyl diazoacetate, we examined the BF 3 ؒ , OEt 2 and TMSCl activation of imines in the ylide reaction for the preparation of vinyl-and ethynylaziridines (eqn 10, Scheme 9). A variety of aromatic aldimines, either N-aryl or N-alkyl, could be aziridinated with good to excellent yields, but aziridination failed when aliphatic aldimines were used as substrates.…”

Section: Aziridination Via Ylide Routementioning

confidence: 99%

Stereoselective synthesis of three-membered ring compounds via ylide routes

Dai¹,

Hou²,

Zhou³

1999

Pure and Applied Chemistry

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Three types of small ring compounds (epoxides, aziridines and cyclopropanes) can be synthesized stereoselectively via ylide route. Among them, the stereochemistry of vinyloxiranes, vinylaziridines, cyclopropylesters, amides and ketones can be tuned by the choice of reaction conditions and ylides with varying heteroatoms and ligands. Optically active epoxides and acetylenylaziridines can be prepared via camphor-derived chiral sulfonium ylide routes.

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Lewis Acid-Catalyzed Synthesis of Aziridines

Cited by 173 publications

References 22 publications

Recentes avanços na preparação de aziridinas. Aplicações sintéticas e implicações mecanísticas

Recentes avanços na preparação de aziridinas. Aplicações sintéticas e implicações mecanísticas

Stereoselective reactions with imines

Stereoselective synthesis of three-membered ring compounds via ylide routes

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