Convenient synthesis of α,β-unsaturated γ-butyrolactones and γ-butyrolactams via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams using 1,3-diiodo-5,5-dimethylhydantoin

Supasorn Phae-NokChutima KuhakarnManat PohmakotrVichai ReutrakulDarunee SoorukramMahidol University2018-11-232018-11-232015-01-01Organic and Biomolecular Chemistry. Vol.13, No.45 (2015), 11087-11095147705202-s2.0-84947460141https://repository.li.mahidol.ac.th/handle/20.500.14594/35520© 2015 The Royal Society of Chemistry. A convenient synthetic approach to α,β-unsaturated γ-butyrolactones and α,β-unsaturated γ-butyrolactams is developed. The reaction proceeds via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams, employing 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation, followed by dehydroiodination of β-iodo-γ-butyrolactones and γ-butyrolactams providing good yields of α,β-unsaturated γ-butyrolactones and γ-butyrolactams, which are synthetically useful building blocks in organic synthesis.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryConvenient synthesis of α,β-unsaturated γ-butyrolactones and γ-butyrolactams via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams using 1,3-diiodo-5,5-dimethylhydantoinArticleSCOPUS10.1039/c5ob01574j