ArticleAngewandte Chemie (International ed. in English)2021
Alkene Isomerization Revitalizes the Coates-Claisen Rearrangement.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed.
- PotassiumACS omega · 2026Article
- NJACS Au · 2024Article
- Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes.Organic letters · 2022Article
- Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring-Opening of 1,1-Biscyclopropyl Methanol Derivatives.Angewandte Chemie (International ed. in English) · 2022Article
- Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters.Journal of the American Chemical Society · 2022Article
- Stereodivergent Access to Trisubstituted Alkenylboronate Esters through Alkene Isomerization.Organic letters · 2021Article
- Alkene Isomerization Revitalizes the Coates-Claisen Rearrangement.Angewandte Chemie (International ed. in English) · 2021Article
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2 authors.
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Abstract
The [3,3]-sigmatropic rearrangement of allylic vinyl acetals, first investigated by Coates nearly four decades ago, is set apart from other variants of the Claisen rearrangement owing to the versatile monoprotected 1,5-dicarbonyl motif featured in the products. Unfortunately, the synthetically elusive nature of the substrates has thus far precluded the widespread application of this attractive transformation. Herein, we show that the key allylic vinyl acetals can be efficiently generated through alkene isomerization of their readily available regioisomeric counterparts (derived from allylic alcohols and α,β-unsaturated aldehydes), thus enabling the first systematic study of the substrate scope of this rearrangement, as well as the discovery of exceptionally mild conditions for its mediation by Lewis and Brønsted acids.
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