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Lewis Acid‐Catalyzed (3+2) Cycloaddition of 2‐Indolylmethanols with β,γ‐Unsaturated α‐Ketoesters

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A Lewis acid-catalyzed (3+2) cycloaddition of 2-indolylmethanols with β,γ-unsaturated α-ketoesters was established. Various cyclopenta[b]indoles were obtained in overall high yields with excellent diastereoselectivities. This reaction not only represents the first C3-nucleophilic (3+2) cycloaddition of 2-indolylmethanols, but also provides a good example for (2+n) cycloaddition of β,γ-unsaturated α-ketoesters.


Abstract

A Lewis acid-catalyzed (3+2) cycloaddition of 2-indolylmethanols with β,γ-unsaturated α-ketoesters was established, which afforded a series of cyclopenta[b]indoles in overall high yields (up to 98 %) with excellent diastereoselectivities (up to >95 : 5 dr). This reaction not only represents the first C3-nucleophilic (3+2) cycloaddition of 2-indolylmethanols, but also provides a good example for (2+n) cycloaddition of β,γ-unsaturated α-ketoesters, which will add new contents to the chemistry of 2-indolylmethanols. In addition, this approach provides an atom-economic and useful method for the construction of biologically important cyclopenta[b]indole scaffold.

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