Catalytic Asymmetric Epoxide Ring‐opening Chemistry
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This chapter contains sections titled: Introduction Enantioselective Nucleophilic Addition to Meso-Epoxides Nitrogen-centered Nucleophiles Sulfur-centered Nucleophiles Oxygen-centered Nucleophiles Carbon-centered Nucleophiles Halide and Hydride Nucleophiles Kinetic Resolution of Racemic Epoxides Nitrogen-centered Nucleophiles Oxygen-centered Nucleophiles Carbon-centered Nucleophiles Enantioselective Rearrangements of Epoxides Conclusion ReferencesDomino
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Reactivity
Butyllithium
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Mannich reaction
Aldol reaction
Hydrocyanation
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Water has proved to be an excellent reaction medium for the definition of highly chemically-efficient and environmentallyfriendly synthetic processes. In several cases, by exploiting the unique properties of water it has been possible to realize more selective and efficient processes than those performed in organic media, including the ring-opening of epoxides by nucleophiles. In this review article the role of water in influencing the stereoselectivity of epoxide ring-opening reactions will be presented, including the most recent examples of enzyme-catalyzed processes. Keywords: Epoxide, water, stereoselective transformations, catalysis, synthetic processes, organic, ring-opening reactions, nucleophiles, species, acids
Organic Synthesis
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A ring made up of eight sulfur and four nitrogen atoms is present in S8N4(SO2CF3)4; this is the largest sulfur-nitrogen ring yet prepared. Its synthesis was at least facilitated, if not made possible, by the electron-withdrawing trifluoro-methanesulfonyl substituent.
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Solvent effect in reaction of 1,3-dimethylthymine epoxide (1) with amines was investigated. The results are summarized in Table I, indicating that the ratio of formation of the cis product (2) increases as a solvent becomes more polar. Reaction of thymidine epoxide (5) with nucleophiles was also examined.
Thymidine
Coupling reaction
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Abstract It is proposed that asymmetric syntheses be divided into enantioselective and diastereoselective syntheses. The enantioselective hydrogenations discussed in the present progress report were catalyzed by Raney nickel that had previously been treated with solutions of optically active compounds. Relationships exist between the enantioselectivity of the catalyst and the structure of the chiral compound used to modify it.
Raney nickel
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The 4‐membered ring in bicyclic azetidiniums, e.g. 1‐azabicyclo[2.n.0]alkanes ( n = 1–4), can be efficiently transformed to larger rings. This minireview focuses on the ring‐expansion of these azetidiniums to five‐ and eight‐membered nitrogen containing heterocycles (pyrrolidines, piperidines, azepanes and azocanes). The ring‐expansion is induced by nucleophiles which can be internal nucleophiles (leaving groups), or external nucleophiles.
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Merging Jørgensen's and MacMillan's organocatalytic aldehyde chlorinations enables the synthesis of chiral vinylcyclopropanes and (−)-cis-aerangis lactoneviaterpene-derived 1,2-epoxides.
Terpene
Carbon fibers
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This review focuses on the enantioselective synthesis of halogenated molecules having a chiral halocarbon center. In particular, this review discusses enantioselective transformations with haloalkenes and enantioselective α-substitutions of α-halo carbonyl compounds. Enantioselective halogen-transfer reactions are excluded from this review.
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