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Chemo‐ and Diastereoselective Epoxidation of Chiral Allylic Alcohols with the Urea Hydrogen Peroxide Adduct, Catalyzed by Titanium Silicate 1
Author(s) -
Adam Waldemar,
Kumar Rajiv,
Reddy T. Indrasena,
Renz Michael
Publication year - 1996
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.199608801
Subject(s) - chemistry , adduct , allylic rearrangement , catalysis , hydrogen peroxide , alcohol , titanium , epoxide , organic chemistry , peroxide , silicate , medicinal chemistry
The threo epoxy alcohol 2 is the major stereoisomer formed in the epoxidation reaction of the chiral allylic alcohol 1 when the zeolite titanium silicate 1 (TS‐1) is employed as heterogeneous catalyst and the urea hydrogen peroxide adduct (UHP) as oxygen source. The hydroxy‐directing effect is rationalized in terms of hydrogen bond formation analogous to that for the mechanism of peracid epoxidation.