Green Organocatalytic Dihydroxylation of Alkenes. Issue 11 (3rd January 2017)

• Record Type: Journal Article
• Authors: Theodorou, Alexis; Triandafillidi, Ierasia; Kokotos, Christoforos G.
• Is Part Of: European journal of organic chemistry. Issue 11(2017)
• Page Start: 1502
• Page End: 1509
• Publication Date: 2017-01-03
• Subjects: Organocatalysis -- Oxidation -- Green chemistry -- Dihydroxylation -- Alkenes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601144
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An inexpensive, green, metal‐free one‐pot procedure for the dihydroxylation of alkenes is described. H2 O2 and 2, 2, 2‐trifluoroacetophenone were employed as the oxidant and organocatalyst, respectively, in this highly sustainable protocol in which a variety of homoallylic alcohols, aminoalkenes, and simple alkenes were converted into the corresponding polyalcohols in good to excellent yields. This process takes advantage of an epoxidation reaction followed by an acidic treatment in which water participates in the ring opening of the in situ prepared epoxide to lead to the desired product. Abstract : One‐pot magic: A green organocatalytic one‐pot procedure for the dihydroxylation of alkenes is described. The reaction proceeds through an intermolecular ring opening of the in situ prepared epoxide in the presence of water to lead to the desired product. A variety of homoallylic alcohols, aminoalkenes, and simple alkenes were converted into the corresponding polyalcohols in excellent yields.