A concise enantioselective synthesis of (+)-endo-brevicomin accomplished by a tellurium/metal exchange reaction

Ferrarini, Renan S.; Princival, Jefferson L.; Comasseto, J. V.; Santos, Alcindo A. Dos

doi:10.1590/s0103-50532008000500002

Cited by 8 publications

(4 citation statements)

References 5 publications

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“…Thus, the N-Boc and N-Cbz β-telluro amines 1a and 1b were prepared in 76 and 78% yields, respectively, by nucleophilic displacement of the mesylate groups of BocHNCH 2 CH 2 OMs 20 and CbzHNCH 2 CH 2 OMs, 21 using n-BuLi and elemental tellurium [BuTeLi] in a mixture of THF and ethanol (Scheme 3, path a). On the other hand, the N-Ts and N-Bz β-telluro amines 1c and 1d were easily obtained via the ring-opening reaction of the corresponding aziridines, 17,22 using the same tellurium nucleophilic species (Scheme 3, path b).…”

Section: Resultsmentioning

confidence: 99%

“…12 These compounds have been efficiently used as alternative organometallic sources of 1,4-dianion intermediates in the synthesis of diols, 13 spiroketals, 14 bioactive butenolides, 15 and in the synthesis of natural products, such as (+/−)-frontalin 16 and (+)-endobrevicomin. 17 In this way, based on the interesting results obtained with the application of oxygen-containing organotellurium compounds [12][13][14][15][16] and following our current interest concerning the development of functionalized alkyl tellurides in organic synthesis, we decided to explore herein…”

Section: Introductionmentioning

confidence: 99%

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N-Functionalized organolithium compounds via tellurium/lithium exchange reaction

Vargas

Toledo

Comasseto

2010

J. Braz. Chem. Soc.

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Um conjunto de amino teluretos foram preparados e testados em reações de troca telúrio/ lítio. Os compostos de organolítio contendo nitrogênio foram facilmente preparados utilizando N-Bz teluroaminas e uma combinação de n-butillítio/naftaleto de lítio nas reações de troca. Os correspondentes intermediários dilitiados foram capturados com vários eletrófilos, levando à formação dos respectivos produtos em bons rendimentos. A reação foi empregada na síntese de fenetilaminas.A set of tellurium amines have been evaluated in the tellurium/lithium exchange reaction. The nitrogen-containing organolithium compounds were efficiently prepared by using N-Bz tellurium amines and a mixture of n-butyllithium and lithium naphthalenide (LiNp) for performing the exchange reaction. The corresponding dianion intermediates were trapped with a wide range of electrophiles, furnishing the corresponding products in good to excellent yields. The reaction was also employed in the synthesis of phenethylamines.Keywords: tellurium/lithium exchange reaction, functionalized organolithium, dianion intermediate, phenethylamines IntroductionOrganolithium compounds are versatile and useful organometallics due to their excellent nucleophilic reactivity and importance in synthetic organic chemistry. 1 Among them, functionalized organolithium compounds represent an important class of intermediates with the ability of transfering the functionality to an electrophilic reagent. In this way, the preparation of functionalized organolithium compounds via halogen/lithium 2 and tin/ lithium 3 exchange reactions represent an interesting protocol of carbon-carbon bond formation for the synthesis of polyfunctionalized molecules, as well as a wide range of natural products. For years, several groups have been interested in the study and preparation of different α-, β-, γ-, δ-oxygen or nitrogen-functionalized organolithium intermediates and their reaction with electrophiles. 4,5 However, among these intermediates, the corresponding β-functionalized compounds, showed to be very unstable species, decomposing via β-elimination to give olefins. 6 On the other hand, organotellurium chemistry is a very broad and exciting field with many opportunities for research and development of applications in organic synthesis.7 Many different classes of organotellurium compounds have been prepared to date and successfully employed in different synthetic applications, 8 as well as in the total synthesis of natural products. 9 Among the several applications of organotellurium compounds, the formation of organolithium compounds via tellurium/ lithium exchange reaction represents an interesting protocol with a number of advantages over alternative methods. 10,11 Our research group has been working in the preparation and application of hydroxy alkyl tellurides in the tellurium/ lithium exchange reaction. 12 These compounds have been efficiently used as alternative organometallic sources of 1,4-dianion intermediates in the synthesis of diols, 13 spiroketals, 14 bioactive butenolides, 1...

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

N-Functionalized organolithium compounds via tellurium/lithium exchange reaction

Vargas

Toledo

Comasseto

2010

J. Braz. Chem. Soc.

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“…Recently, our research group has been working in the preparation and application of hydroxy tellurides in the tellurium/lithium exchange reaction. These compounds have been efficiently used as alternative organometallic sources of 1,4-dianion intermediates in the synthesis of diols [8], spiroketals [9], bioactive butenolides [10], and in the synthesis of natural products, such as (±)-frontalin [11] and (+)-endo-brevicomin [12]. The interesting results obtained with oxygen-containing organotellurium compounds served as inspiration for the design and application of many other functionalized organotellurium compounds.…”

Section: Introductionmentioning

confidence: 99%

“…In this way, following our current interest in the development and application of functionalized organotellurium compounds in organic synthesis [8][9][10][11][12], we report herein the preparation of a modular series of nitrogen-containing organotellurium compounds and their selenium and sulfur analogues via the ring-opening reaction of easily available aziridines, as depicted in Fig. 1.…”

Section: Introductionmentioning

confidence: 99%

Practical synthesis of chiral β-telluro amines by ring-opening reaction of aziridines

Vargas

Comasseto

2009

Journal of Organometallic Chemistry

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Tellurium in organic synthesis: the enantioselective synthesis of the pheromone blend components of Mayetiola destructor, Drosophila mulleri and Contarinia pisi

Ferrarini

Comasseto

Santos

2009

Tetrahedron: Asymmetry

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A concise enantioselective synthesis of (+)-endo-brevicomin accomplished by a tellurium/metal exchange reaction

Cited by 8 publications

References 5 publications

N-Functionalized organolithium compounds via tellurium/lithium exchange reaction

N-Functionalized organolithium compounds via tellurium/lithium exchange reaction

Practical synthesis of chiral β-telluro amines by ring-opening reaction of aziridines

Tellurium in organic synthesis: the enantioselective synthesis of the pheromone blend components of Mayetiola destructor, Drosophila mulleri and Contarinia pisi

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