ArticleNature chemistry2026
The catalytic enantioselective [1,2]-Wittig rearrangement cascade of allylic ethers.
Article in Nature chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Molecular rearrangements as powerful tools in diversity-oriented natural products synthesis: a review.RSC advances · 2026Review
- The Catalytic Enantioselective Sommelet-Hauser Rearrangement.Journal of the American Chemical Society · 2026Article
- Catalytic Enantioselective Dearomatizing [2,3]-Wittig Rearrangements Allow Divergent [2,3]-, [1,2]-, and Sommelet-Hauser-Type Products.Journal of the American Chemical Society · 2026Article
- Graph-Based Internal Coordinate Analysis for Transition State Characterization.Journal of chemical theory and computation · 2026Article
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Authors and funding
11 authors.
Funding
Abstract
The catalytic enantioselective [1,2]-Wittig rearrangement of allylic ethers constitutes a recognized synthetic challenge as it is traditionally considered to arise from a non-concerted reaction pathway via formation and recombination of radical pairs. Here we show a catalytic enantioselective solution to this challenge, demonstrating that [1,2]-Wittig products are generated via an alternative reaction cascade to traditional dogma. The developed process employs a chiral bifunctional iminophosphorane catalyst to promote an initial enantioselective [2,3]-sigmatropic rearrangement. A subsequent base-promoted, stereoconvergent, fragmentation-recombination process that proceeds with high enantiospecificity and retention of configuration, formally equivalent to a Woodward-Hoffmann forbidden thermal [1,3]-sigmatropic rearrangement, generates [1,2]-Wittig products in up to 97:3 enantiomeric ratio. Supported by extensive quantum chemistry calculations, this chirality transfer process will have broad implications for fundamental stereocontrol in organic transformations.
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Registered trials
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