Orthogonally Protected 1,2-Diols from Electron-Rich Alkenes Using Metal-Free Olefin syn-Dihydroxylation

Autor(es)

Colomer, Ignacio ; Barcelos, Rosimeire Coura ; Christensen, Kirsten E. ; Donohoe, Timothy J.

• Tipo de documento: Artigo Científico
• Fonte: ORGANIC LETTERS; v. 18, n. 22, p. 5880-5883, NOV 18 2016.
• Citações Web of Science: 13

Resumo

A new method for the stereoselective metal-free syn-dihydroxylation of electron-rich olefins is reported, involving reaction with TEMPO/IBX in trifluoroethanol (TFE) or hexafluoroisopropanol (HFIP) and the addition of a suitable nucleophile. Orthogonally protected syn 1,2-diols were obtained with high levels of diastereocontrol, and these products were selectively deprotected and selectively functionalized into synthetically useful compounds. (AU)

• Processo FAPESP: 14/16516-9 - Novas reações catalíticas para a construção de peptídeos e híbridos de carboidratos
• Beneficiário: Rosimeire Coura Barcelos
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Pós-Doutorado