Sulfur-ylide-mediated synthesis of functionalized and trisubstituted epoxides with high enantioselectivity; application to the synthesis of CDP-840.
نویسندگان
چکیده
منابع مشابه
The complexity of catalysis: origins of enantio- and diastereocontrol in sulfur ylide mediated epoxidation reactions.
The reaction of chiral sulfur ylides with aldehydes and ketones has emerged as a useful asymmetric process for the synthesis of epoxides. Processes employing either catalytic or stoichiometric amounts of sulfides have been developed. Although a large number of chiral sulfur ylides have been tested in the epoxidation process, only a few have delivered high diastereo- and enantio- selectivity. Th...
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Heating one of the most abundant naturally occurring inorganic chemicals (elemental sulfur) with one of the most readily available homochiral molecules (limonene) gives a one-step synthesis of a chiral sulfide which exhibits outstanding selectivities in sulfur ylide mediated asymmetric epoxidations and aziridinations. In particular reactions of benzyl and allylic sulfonium salts with both aroma...
متن کاملCatalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: scope, selectivity, and applications in synthesis.
The reaction of sulfur ylides with carbonyl compounds to give epoxides is an important synthetic method. This Account charts the recent advances in rendering this process both asymmetric and catalytic. Two catalytic methods have been developed: the first involving the reaction of a sulfide with an alkyl halide in the presence of a base and aldehyde and the second involving the reaction of a sul...
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Background: Enantiopure epoxides are important intermediates in the synthesis of high-value chiral chemicals. Epoxide hydrolases have been exploited in biocatalysis for kinetic resolution of racemic epoxides to produce enantiopure epoxides and vicinal diols. It is necessary to obtain sufficient stable epoxide hydrolases with high enantioselectivity to meet the requirements of i...
متن کاملHighly enantioselective ylide-mediated synthesis of terminal epoxidesw
The importance of chiral epoxides as synthetic building blocks in asymmetric synthesis is extremely difficult to overstate. While the highly enantioselective Sharpless, and JacobsenKatsuki, protocols for the epoxidation of internal alkenes are nowmature technologies of inestimable value, the conversion of terminal alkenes to enantioenriched 1-oxiranes has proven a considerably more difficult pr...
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ورودعنوان ژورنال:
- Angewandte Chemie
دوره 42 28 شماره
صفحات -
تاریخ انتشار 2003