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Practical and Rapid Vicinal Hydroxylation of Alkenes by Catalytic Ruthenium Tetraoxide
Author(s) -
Shing Tony K. M.,
Tai Vincent W.F.,
Tam Eric K. W.
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199423121
Subject(s) - chemistry , hydroxylation , vicinal , ruthenium , catalysis , acetonitrile , organic chemistry , diol , solvent , medicinal chemistry , enzyme
Within minutes simple olefins, α,β‐unsaturated ketones and esters, allyl acetates, and allyl benzyl ethers can be cis ‐dihydroxylated. The oxidation, an extension of Sharpless's method, is conducted with 0.07 equivalents of RuCl 3 ·3H 2 O and 1.5 equivalents of NaIO 4 in a two‐phase solvent system consisting of ethyl acetate, acetonitrile, and water at 0 °C! The low extent of diol cleavage and ketol formation is surprising.