AI Article Synopsis
- This study introduces a novel method for the kinetic resolution of carbon nucleophiles using Pd-catalyzed asymmetric allylic alkylation with unstabilized ketone enolates.
- The process successfully yields both allylated 2,3-disubstituted 2,3-dihydro-4-quinolones and allows for the recovery of starting materials with high yields and enantiomeric excess (ee).
- The practical application of this methodology in organic synthesis is highlighted by the conversion of the allylated product into pyrrolo[3,2-c]quinoline, which is related to the structure of active Martinella alkaloids.
Article Abstract
The kinetic resolution of a carbon nucleophile is realized for the first time via Pd-catalyzed asymmetric allylic alkylation with "unstabilized" ketone enolates as the nucleophile, providing both allylated 2,3-disubstituted 2,3-dihydro-4-quinolones and recovered substrates in high yields and high ee (S-factor is 40-145). The application of the methodology in organic synthesis is demonstrated by the ready transformation of an allylated adduct into pyrrolo[3,2-c]quinoline, which features a core structure of biologically active Martinella alkaloids.
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| http://dx.doi.org/10.1021/ja9082717 | DOI Listing |
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