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Synthesis of syn and anti 1,4‐Diols by Copper‐Catalyzed Boration of Allylic Epoxides
Author(s) -
Tortosa Mariola
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201100613
Subject(s) - allylic rearrangement , diol , chemistry , catalysis , copper , alcohol , organic chemistry
Two sides of the same coin : Syn and anti 1,4‐diols have been synthesized through the regio‐ and diastereoselective Cu I ‐catalyzed boration of allylic epoxides (see scheme; pin=pinacolato, TES=triethylsilyl). In situ protection of the alcohol allows isolation of syn and anti 1,4‐silyloxyboronates. Monoprotected 1,4‐diols can be prepared by a one‐pot addition–protection–oxidation sequence.
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