- A Novel Cycloaromatization Reaction. Regiocontrolled Synthesis of Substituted Methyl Salicylates
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A new method of constructing six-membered rings, involving the condensation of two three-carbon units, one with two nucleophilic sites and the other containing two electrophilic sites, is reported.The regiochemistry of the reaction is controlled by the differential reactivities of these sites. 1,3-Bis(trimethylsiloxy)-1-methoxybuta-1,3-diene (1) constitutes the three-carbon fragment with two nucleophilic sites.Condensation of 1 with various equivalents of β-dicarbonyl compounds and titanium tetrachloride gave substituted methyl salicylates.The regiochemistry is controlled by the order of reactivity of the electrophilic sites, which is conjugate position of enone > ketone > monothioacetal, acetal.
- Chan, Tak-Hang,Brownbridge, Peter
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- Asymmetrie ruthenium-catalyzed 1,4-additions of aryl thiols to enones
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Well defined, stable, one-point binding ruthenium complexes 1 and 2 selectively bind and activate α,β-unsaturated carbonyl compounds for cycloaddition reactions. These mild Lewis acids catalyze asymmetric 1,4-addition reactions of aryl thiols to enones wi
- Badoiu, Andrei,Bernardinelli, Gerald,Besnard, Celine,Peter Kuendig
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supporting information; experimental part
p. 193 - 200
(2010/04/25)
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