Synthesis of enantiomerically pure substituted tetrahydrofurans from epoxides and phenylselenium reagents

Enzymatic resolution of (RS)-β-hydroxy selenides in organic media

“…4 With the aim of combining the synthetic potential of the biocatalysis with the organoselenium chemistry, we initiated a program to apply biocatalysis in the preparation of enantiopure chiral selenium organic compounds. 5 The selanyl group of bhydroxy selenides can be used in radical carbon-carbon bond formation, especially the intramolecular type (radical cyclizations), 6 which is useful for synthesis of organic molecules. 7 Lipases tolerate unnatural substrates and reaction conditions very well and are ideal candidates to explore possibilities to prepare enantiopure selenium compounds in transesterification reactions in organic media.…”

New Developments with Chiral Electrophilic Selenium Reagents

“…Camphor-based diselenides such as 13 [58][59][60][61][62] have been prepared as well. Based on the success of diselenides 14 and 15, structural variants 17 [63,64] and diselenides with different coordinating heteroatoms such as sulfur 18 [65][66][67][68][69][70][71][72] and selenium 19 [73] have been described recently.…”

Enantioselective synthesis of heterocyclic compounds mediated by organoselenium reagents

“…Thus all the possible eight isomers of 2,5-dimethyl-3-phenyl tetrahydrofurans were prepared in an enantiomerically pure form. 19 An example of the combined use of the reactivity of organoselenium reagents to promote cyclization reactions is reported in Scheme 10 which refers to the synthesis of perhydrofuro[3,4-b]pyrans and of perhydrofuro[3,4-b]furans. 20 The ylide deriving from benzyl bromide was made to react with the D-glyceraldehyde acetonide 37.…”