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Synfacts 2007(8): 0823-0823  
DOI: 10.1055/s-2007-968734
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Titanium-Mediated Olefin Epoxidation Using Hydrogen Peroxide

Contributor(s): Mark Lautens, Michael Langer
Y. Sawada, K. Matsumoto, T. Katsuki*
Kyushu University, Fukuoka, Japan
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

Enantioenriched epoxides are versatile intermediates in organic synthesis. The synthetic methods developed so far often involve oxidants of low atom economy or require the use of activated substrates. The authors found that di-µ-oxo titanium(salalen) complex 1 epoxidizes conjugated olefins with high TON in the presence of hydrogen peroxide as oxidant. They extended the methodology to unactivated olefins bearing only alkyl groups on the alkene. See also previous work: Angew. Chem. Int. Ed. 2005, 44, 4935; Angew. Chem. Int. Ed. 2006, 45, 3478.