Remote chiral induction in vinyl sulfonium salt-mediated ring expansion of hemiaminals into epoxide-fused azepines.
نویسندگان
چکیده
منابع مشابه
Hemiaminals as substrates for sulfur ylides: direct asymmetric syntheses of functionalised pyrrolidines and piperidines.
Phenyl stabilised chiral sulfur ylides react with five-membered-ring hemiaminals to give functionalised pyrrolidines directly with high enantioselectivity. The reaction can be diverted to give piperidines instead by isolation of the intermediate epoxide and treatment with TMSOTf.
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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...
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The 3-azabicycloACHTUNGTRENNUNG[3.1.0]hexane is a common motif in natural products. Furthermore this rigid framework represents a privileged class of pharmacologically active compounds, often showing enhanced binding affinities with their targets (Figure 1). These bicycles also represent conformationally restricted analogues of piperidines (e.g. trovafloxacin). When substituted with a carboxyli...
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An efficient and diastereoselective strategy based on an intramolecular domino aza-Michael/Darzens reaction to synthesize epoxide-fused benzoquinolizidines has been described. Three bonds (1 C-C, 1 C-N and 1 C-O), three rings and three chiral centers can be constructed in a single pot under very mild conditions. All the products were isolated in only one diastereomer with 40-80% yields.
متن کاملAn efficient synthesis of imidazolinium salts using vinyl sulfonium salts.
The synthesis of imidazolinium salts from the reaction of formamidines and (2-bromoethyl)diphenylsulfonium triflate is described. A variety of symmetrical and unsymmetrical imidazolinium triflate salts were synthesized in high yield in short reaction times under mild conditions. Aromatic and aliphatic N-substituents work well. The reaction is proposed to proceed via generation of a vinyl sulfon...
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عنوان ژورنال:
- Chemistry, an Asian journal
دوره 6 2 شماره
صفحات -
تاریخ انتشار 2011