Journal
SYNTHESIS-STUTTGART
Volume -, Issue 15, Pages 2567-2573Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2004-831207
Keywords
epoxides; titanium; reductive ring opening; H-atom donors; gamma-terpinene
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Novel hydrogen atom donors for the reductive titanocene-catalyzed epoxide opening are presented. While the potentially attractive cyclopentadienes gave only moderate yields of the desired alcohols, substituted, nontoxic, and commercially available 1,4-cyclohexadienes, e.g. gamma-terpinene, in combination with more elaborate catalysts gave better or similar results than the much more expensive and carcinogenic 1,4-cyclohexadiene. In the practically important reactions of Sharpless epoxides and their derivatives excellent levels of regioselectivity for the epoxide opening could be obtained. The toxic and unpleasant to handle tert-butyl thiol could be replaced while increasing the yields of the desired products.
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