ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
A Nazarov-Ene Tandem Reaction for the Stereoselective Construction of Spiro Compounds.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. 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.
- Recent advances in total synthesis of illisimonin A.Beilstein journal of organic chemistry · 2025Review
- Asymmetric Total Synthesis of Illisimonin A.Journal of the American Chemical Society · 2023Article
- A Nazarov-Ene Tandem Reaction for the Stereoselective Construction of Spiro Compounds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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Abstract
The different reactivity of trienones under Lewis and Brønsted acids catalysis was investigated, resulting in distinct cyclization products and carbon backbones that originated either from a conjugate Prins cyclization or an interrupted Nazarov cyclization. In particular, an unprecedented Nazarov cyclization tandem reaction is presented, terminating the oxyallyl cation by an ene-type reaction, and leading stereoselectively to bicyclic spiro compounds. The terminal olefin of this motif represents a useful handle for further functionalization, making it a strategic intermediate in total syntheses. The tandem Nazarov/ene cyclization was shown to be preferred over a Nazarov/[3+2] tandem reaction for all our substrates, independent of chain length. Deuteration studies further support the mechanistic hypothesis of the terminating ene reaction.
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