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

Vargas, Fabrı́cio; Comasseto, J. V.

doi:10.1016/j.jorganchem.2008.09.025

Cited by 14 publications

(5 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Vargas and Comasseto reported the synthesis of chiral βtelluroamines via the NROR of N-Boc and N-Ts protected aziridines with lithium organotellurolates, in situ generated from elemental tellurium and organolithium compounds (Scheme 9). 22 The authors found this method to be more efficient with respect to generating tellurium nucleophiles by reduction of ditellurides or by insertion of a tellurium into carbon-magnesium bonds. The same procedure could also be applied to the synthesis of related aminoselenides and aminosulfides.…”

Section: Synthesis Of Unsymmetric Selenides and Telluridesmentioning

confidence: 99%

Ring opening reactions of heterocycles with selenium and tellurium nucleophiles

Tanini

Capperucci

2019

New J. Chem.

View full text Add to dashboard Cite

show abstract

Section: Synthesis Of Unsymmetric Selenides and Telluridesmentioning

confidence: 99%

Ring opening reactions of heterocycles with selenium and tellurium nucleophiles

Tanini

Capperucci

2019

New J. Chem.

View full text Add to dashboard Cite

show abstract

“…The preparation of the corresponding nitrogencontaining organotellurium compounds was described in our previous communication, 18 via the ring-opening reaction of aziridines by tellurium nucleophiles generated in situ, as depicted in Scheme 1. All the β-organotellurium amines, bearing different steric and electronic characteristics, were obtained in up to 89% yield and under very mild conditions.…”

Section: Resultsmentioning

confidence: 99%

N-Functionalized organolithium compounds via tellurium/lithium exchange reaction

Vargas

Toledo

Comasseto

2010

J. Braz. Chem. Soc.

Self Cite

View full text Add to dashboard Cite

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...

show abstract

“…Symmetrical dialkyl tellurides and ditellurides are commonly prepared through the reaction of alkali tellurides and ditellurides with haloalkanes or alkyl tosylates . Other methods involve the insertion of tellurium into the carbon−metal bond of organolithium compounds or Grignard reagents . Further functionalisable β‐halo dialkyl tellurides and ditellurides can be accessed from terminal alkenes and tellurium tetrahalides .…”

Section: Introductionmentioning

confidence: 99%

“…[2a,18] Other methods involve the insertion of tellurium into the carbonÀ metal bond of organolithium compounds or Grignard reagents. [2,19] Further functionalisable β-halo dialkyl tellurides and ditellurides can be accessed from terminal alkenes and tellurium tetrahalides. [20] In this context, despite their interest, tellurides and ditellurides bearing O-and N-containing functionalities have been scarcely explored.…”

Section: Introductionmentioning

confidence: 99%

Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

2020

View full text Add to dashboard Cite

The on water reaction of sodium telluride with electrophiles has been explored. Na2Te, generated in situ through the rongalite (sodium hydroxymethanesulfinate)‐promoted reduction of elemental tellurium, reacts with a wide variety of electrophiles, including strained heterocycles, haloalkanes, Michael acceptors, and aryl diazonium salts, providing simple and rapid access to a broad range of novel functionalised symmetrical tellurides. The methodology well tolerated the presence of versatile functional groups such as alchohols, amines, esters, nitriles, and sulfones and allowed the incorporation of tellurium atoms into biologically relevant natural‐derived products. Furthermore, in the case of the nucleophilic ring opening of epoxides and aziridines, a judicious tuning of the reaction conditions enabled the synthesis of unreported β‐hydroxy‐ and β‐amino‐ditellurides, which were further employed as precursors of new functionalised unsymmetrical dialkyl tellurides. The thiol−peroxidase catalytic activity of hydroxy‐ditellurides has also been investigated in order to compare their antioxidant properties with those of homologous tellurides.

show abstract

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

Cited by 14 publications

References 26 publications

Ring opening reactions of heterocycles with selenium and tellurium nucleophiles

Ring opening reactions of heterocycles with selenium and tellurium nucleophiles

N-Functionalized organolithium compounds via tellurium/lithium exchange reaction

Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

Contact Info

Product

Resources

About