Highly Efficient One-Step Conversion of Selenol Esters into Symmetrical Diselenides in the Presence of Elemental Iodine in Methanolic Solution

Movassagh, Barahman; Moradi, Mona

doi:10.1080/10426500902753379

Cited by 3 publications

(1 citation statement)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[9][10][11] Selenoesters also can be applied to new materials design, including liquid crystals [12][13][14] and responsive polymers. [15] In organic synthesis, selenoesters was already described as protecting groups, [16] and successfully applied in reactions with diazomethane, [17,18] Diels-Alders reaction, [19][20][21] synthesis of selenides, [22] and diselenides [23,24] and heterocycles compounds. [25,26] However, the main use of selenoesters in organic synthesis is acyl donor.…”

Section: Introductionmentioning

confidence: 99%

Exquisite use of Selenoesters as Recyclable Acyl Donors for Lipases‐catalyzed Kinetic Resolution

et al. 2022

View full text Add to dashboard Cite

Lipase‐catalyzed enantioselective synthetic reactions employing enol esters, activated esters, anhydrides, and oximes as acyl donors is a well‐consolidated strategy towards enantiopure compounds. However, lipases can also cleave the C−S bond of thioesters, proving that other classes of substances can be used as acyl donors in lipase‐catalyzed transformations. Herein we describe the application of selenoesters as a new class of acyl donors in enzymatic kinetic resolution of chiral alcohols. A series of selenoesters was successfully employed in the resolution of chiral primary and secondary alcohols, demonstrating that lipases can also cleave the C−Se bond. Assays using selenoesters as acyl donors in lipase‐catalyzed reactions furnished enantiopure compounds (e.e.>99 %) and enantiomeric ratio (E>200). We also observed that the enzymatic reaction is accelerated in an oxygen atmosphere and performing a preparative scale reaction could demonstrate how simple and easy the purification process is to recover the diselenide formed during the resolution.

show abstract

Section: Introductionmentioning

confidence: 99%

Exquisite use of Selenoesters as Recyclable Acyl Donors for Lipases‐catalyzed Kinetic Resolution

et al. 2022

View full text Add to dashboard Cite

show abstract

Synthetic Approaches to Selenoesters

Baldassari

Lüdtke

2021

Chemistry A European J

View full text Add to dashboard Cite

Selenoesters are compounds of great synthetic relevance since they can be used in several types of chemical transformations and mainly due to their great capacity in the formation of acyl radicals. Therefore, the scientific community has been developing several methods for the synthesis of this class of molecules. This review will address the synthesis of these compounds from different starting materials, such as carboxylic acids derivatives (acid chlorides and anhydrides), aldehydes, selenoacetylenes and miscellaneous methods.

show abstract

Iodine-catalyzed transformation of molecules containing oxygen functional groups

2011

View full text Add to dashboard Cite

Highly Efficient One-Step Conversion of Selenol Esters into Symmetrical Diselenides in the Presence of Elemental Iodine in Methanolic Solution

Cited by 3 publications

References 29 publications

Exquisite use of Selenoesters as Recyclable Acyl Donors for Lipases‐catalyzed Kinetic Resolution

Exquisite use of Selenoesters as Recyclable Acyl Donors for Lipases‐catalyzed Kinetic Resolution

Synthetic Approaches to Selenoesters

Iodine-catalyzed transformation of molecules containing oxygen functional groups

Contact Info

Product

Resources

About