ArticleOrganic letters2014
Synthesis of isochromene-type scaffolds via single-flask Diels-Alder-[4 + 2]-annulation sequence of a silyl-substituted diene with menadione.
Article in Organic letters, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Journey on Naphthoquinone and Anthraquinone Derivatives: New Insights in Alzheimer's Disease.Pharmaceuticals (Basel, Switzerland) · 2021Review
- Boron and Silicon-Substituted 1,3-Dienes and Dienophiles and Their Use in Diels-Alder Reactions.Molecules (Basel, Switzerland) · 2020Review
- Palladium mediated domino reaction: synthesis of isochromenes under aqueous medium.RSC advances · 2019Article
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Authors and funding
2 authors.
Funding
Abstract
A sequential Diels-Alder reaction/silicon-directed [4 + 2]-annulation was developed to assemble hydroisochromene-type ring systems from menadione 2. In the first step, a Diels-Alder of the 1-silyl-substituted butadiene 1 with 2 furnished an intermediate cyclic allylsilane. Subsequently, TMSOTf promoted a [4 + 2]-annulation through trapping of an oxonium, generated by condensation between an aldehyde and the TBS protected alcohol resulted in the formation of a cis-fused hydroisochromene 13.
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