Synthesis of oxabicyclo[3.3.1]nonenes and substituted tetrahydropyrans via (3,5)-oxonium-ene reaction.
نویسندگان
چکیده
An efficient methodology for the synthesis of oxabicyclo[3.3.1]nonenes and substituted tetrahydropyrans has been developed in moderate yields from the reaction of geraniol with aldehydes and epoxides promoted by boron trifluoride etherate.
منابع مشابه
Synthesis of 2,3,5,6-tetrasubstituted tetrahydropyrans via (3,5)-oxonium-ene reaction.
An efficient method for the synthesis of 2,3,5,6-tetrasubstituted tetrahydropyrans has been developed from the reaction of aldehydes and ethyl 2-(1-hydroxyalkyl/hydroxy(phenyl)methyl)-5-methylhex-4-enoate using (3,5)-oxonium-ene reaction promoted by boron trifluoride etherate in good yields under mild conditions.
متن کاملAu(I)-catalyzed synthesis of 8-oxabicyclo[3.2.1]oct-2-enes and 9-oxabicyclo[3.3.1]nona-2,6-dienes from enynol via oxonium/Prins-type cyclization.
A sustainable and simple Au(I) catalytic system to synthesise 8-oxabicyclo[3.2.1]oct-2-enes and 9-oxabicyclo[3.3.1]nona-2,6-dienes from enynol via oxonium/Prins-type cyclization is described. The key advantages of this reaction are selectivity, good functional group tolerance and a new approach for synthesis of oxabicyclic and oxatricyclic systems.
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2,4,6-Triisopropylstryrene was synthesized in a single step via the Witting Reaction from the corresponding aldehyde. The reaction of three styrene's derivatives, 2,6-dimethylstyrene, 2,4,6-trimethylstyrene, and 2,4,6- triisopropylstyrene with 4-methyl-l,2,4-triazoline-3,5-dion(M eTD) was investigated. These reactions are instantaneous at room temperature and lead to the formation of 2: 1 ...
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Dirhodium catalyzed reactions of aryl-substituted tetrahydropyranone diazoacetoacetates produce ylide intermediates that unexpectedly yield two oxabicyclo[4.2.1]-nonane diastereoisomers, but a single diastereoisomer is formed by increasing the steric bulk of the aryl substituent.
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عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 9 12 شماره
صفحات -
تاریخ انتشار 2011