A Regio- and Stereodivergent Synthesis of <i>v</i><i>ic</i>-Amino Alcohols

Olofsson, Berit; Khamrai, Uttam; Somfai, Peter

doi:10.1021/ol006736i

Cited by 45 publications

(22 citation statements)

References 26 publications

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“…A reação de Mitsunobu intramolecular de β-aminoálcoois vem sendo estudada como uma metodologia direta na obtenção de vinilaziridinas. A abertura do epóxido quiral 13 com amônia (sob microondas) seguida de ciclização do aminoálcool 14 promovida por trifenilfosfina e azodicarboxilato de isopropila (DIAD) fornece a vinilaziridina 15 em bons rendimentos e condições brandas 36,37 (Esquema 7). A vinilaziridina 15 e análogos, como 16, participam em diversas transformações sintéticas valiosas, incluindo a preparação de aminoálcoois com regio-e estereosseletividade invertidas, bem como a transformação para lactamas 37,38 (Esquema 8).…”

Section: (Esquema 2)unclassified

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: (Esquema 2)unclassified

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

Bisol¹,

Sá²

2007

Quím. Nova

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“…Small-scale reactions were purified to give aziridine 2 in 80% yield, whereas large-scale reactions gave 2 in 70% yield. 15 In an attempt to avoid the tedious purification, polymer bound triphenylphosphine was used. As expected, this decreased the reaction rate, but gave an easily purified crude product.…”

Section: Direct Ring-closurementioning

confidence: 99%

Synthesis of N–H vinylaziridines: a comparative study

2002

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Abstract-Vinylaziridines are useful and versatile synthetic intermediates, as the relief of ring-strain provides a driving force for efficient ring-opening or ring-expansion reactions. Furthermore the vinyl group can be derivatized into interesting functionalities. The ring-closure of vicinal amino alcohols constitutes a straightforward route to aziridines. Several methods exist for this transformation, although many cannot be applied to vinylaziridines due to their acid lability. This comparative study describes the most effective sequences for the formation of N-H vinylaziridines.

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“…Acyl aziridines could rearrange to oxazolines through a ring expansion reaction [25][26][27][28][29]. The ring expansion of N-acyl aziridines to oxazolines can be promoted by thermal, acidic, or nucleophilic conditions [30][31][32][33][34][35][36][37][38].However, catalytic examples for the synthesis of oxazolines are rare [39]. Here we report synthesis of N-acyl ketoaziridines from the corresponding ketoaziridines with acyl chlorides.…”

mentioning

confidence: 99%

K5[PW11ZnO39].23H2O-catalyzed acylation/ring expansion of ketoaziridines in a single pot: a new regio- and stereo-selective route for the synthesis of oxazolines

2015

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and synthesis of the derivatives of serines as a antibiotics [13] synthesis of N-hydroxy-N-amino acids [14] and as starting material in the synthesis of the neurotrophic factor Lactacystin [15,16]. Moreover, various oxazolines with biological activity have been isolated from marine organisms [17,18].For many years, several synthetic methods have been described for the synthesis of oxazolines [19][20][21][22]. On the other hand, Aziridines are also well known as useful reagents for the synthesis of many categories of nitrogencontaining compounds, in particular N-heterocycles compounds such as oxazolines, thiazolidinones, thiazolidine thiones, and imidazolidinones [23].Among the synthetic applications of these compounds, the rearrangement of N-activated aziridines has become the object of attention only very recently [24]. Acyl aziridines could rearrange to oxazolines through a ring expansion reaction [25][26][27][28][29]. The ring expansion of N-acyl aziridines to oxazolines can be promoted by thermal, acidic, or nucleophilic conditions [30][31][32][33][34][35][36][37][38].However, catalytic examples for the synthesis of oxazolines are rare [39]. Here we report synthesis of N-acyl ketoaziridines from the corresponding ketoaziridines with acyl chlorides. Then N-acyl ketoaziridines in the presence of a nucleophilic and Lewis acids afforded oxazolines [40][41][42].Although a few methods have been described for the preparation of N-acyl aziridines none of them described direct synthesis of oxazolines from N-H aziridines with carboxylic acid .In continuation of our recent interest in the reaction of ketoaziridines [48] and success for using Polyoxometalates [49], herein, we report a one-pot regio-and stereo-selective synthesis of trans-4-benzoyloxazolines, catalyzed by the K 5 [PW 11 ZnO 39 ].23H 2 O catalytic system with moderate to good yields under mild conditions. Abstract A new and one-pot synthesis of oxazolines has been accomplished by K 5 [PW 11 ZnO 39 ].23H 2 O-catalyst acylation followed by C-N ring opening/C-O bond formation in NH ketoaziridines. This regio-and stereo-selective reaction presumably proceeds via a domino sequence resulting in the in situ generation of acyl aziridine which undergoes a ring expansion reaction via an initial C-N rupture of aziridine ring followed by ring closure to the oxazolines. The methodology provided novel one-pot procedure for the synthesis of trans-2,5-diaryl-4-aroyloxazolines.

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A Regio- and Stereodivergent Synthesis of vic-Amino Alcohols

Cited by 45 publications

References 26 publications

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

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

Synthesis of N–H vinylaziridines: a comparative study

K5[PW11ZnO39].23H2O-catalyzed acylation/ring expansion of ketoaziridines in a single pot: a new regio- and stereo-selective route for the synthesis of oxazolines

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