AI Article Synopsis
- The study presents a method for dearomatizing 3-NO-indoles using phosphine catalysts, yielding densely functionalized indolines efficiently (up to 96% yield).
- The reaction occurs under mild conditions, making it more practical for real-world applications.
- Computational simulations helped elucidate a stepwise mechanism that explains the observed diastereoselection in the products.
Article Abstract
The stereoselective phosphine-catalyzed (( pMeOCH)P, 10-20 mol %) dearomatization of 3-NO-indoles with allenoates is described. A range of densely functionalized indolines (18 examples) is obtained in high yields (up to 96%) under mild reaction conditions (rt, air, reagent-grade solvent). Computational simulations and labeling experiments revealed a stepwise [3 + 2]-type mechanism involving a water-assisted hydrogen shift and accounted for the diastereoselection recorded.
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| http://dx.doi.org/10.1021/acs.joc.9b00559 | DOI Listing |
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