Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 69, Issue 24, Pages 8372-8381Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo048519r
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A new route to diverse 2-substituted-3-methoxycarbonyl pyrroles has been developed. Diverse SES protected alpha-methylene beta-aminoesters were obtained by a 3-component aza-Baylis-Hillman reaction. Diversity arose from the aryl aldehydes which can be used in this reaction. N-Alkylation with allyl bromide under mild conditions provided the corresponding dienes. These substituted dienes were cyclized by ring closing metathesis at room temperature or under microwave-activation with Grubbstype II catalyst to yield SES-protected pyrroline intermediates. The final pyrroles were obtained by base-promoted dehydrodesulfinylation/aromatization., The scope of each of these reactions was explored.
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