33683-44-2Relevant academic research and scientific papers
Catalytic enantioselective peroxidation of α,β-unsaturated ketones
Lu, Xiaojie,Liu, Yan,Sun, Bingfeng,Cindric, Brittany,Deng, Li
supporting information; body text, p. 8134 - 8135 (2009/02/02)
Despite the potential of chiral peroxides as biologically interesting or even clinically important compounds, no catalytic enantioselective peroxidation has been reported. With a chiral catalyst not only to induce enantioselectivity but also to convert a well established epoxidation pathway into a peroxidation pathway, the first efficient catalytic peroxidation has been successfully developed. Employing readily available α,β-unsaturated ketones and hydroperoxides and an easily accessible cinchona alkaloid catalyst, this novel reaction will open new possibilities in the asymmetric synthesis of chiral peroxides. Under different conditions a highly enantioselective epoxidation with the same starting materials, reagents, and catalyst has was also established. Copyright
Phosphine-catalyzed hydration and hydroalkoxylation of activated olefins: Use of a strong nucleophile to generate a strong base
Stewart, Ian C.,Bergman, Robert G.,Toste, F. Dean
, p. 8696 - 8697 (2007/10/03)
The direct addition of water and a variety of alcohols to activated olefins was observed in the presence of nucleophilic phosphine catalysts. Unlike existing methods, the reactions proceed at room temperature and in the absence of transition metals, or strong acids or bases. The use of simple commercially available catalysts makes this an attractive method for the preparation of β-hydroxy and β-alkoxy substrates, which are prevalent targets and intermediates in organic synthesis. The scope and mechanism of this reaction has been explored, and the compound that acts as the resting state of the catalyst was synthesized independently. Our mechanism also suggests the possibility of extending the scope of this reactivity to other classes of nucleophiles. Copyright
