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Green Organocatalytic Dihydroxylation of Alkenes
Author(s) -
Theodorou Alexis,
Triandafillidi Ierasia,
Kokotos Christoforos G.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601144
Subject(s) - dihydroxylation , chemistry , epoxide , organic chemistry , green chemistry , hydroxylation , catalysis , reaction conditions , combinatorial chemistry , enantioselective synthesis , reaction mechanism , enzyme
An inexpensive, green, metal‐free one‐pot procedure for the dihydroxylation of alkenes is described. H 2 O 2 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.