Palladium-Catalyzed Stereoselective Construction of 1,3-Stereocenters Displaying Axial and Central Chirality via Asymmetric Alkylations

The concurrent construction of 1,3-stereocenters remains a challenge. Herein, we report the development of stereoselective union of a point chiral center with allenyl axial chirality in 1,3-position by Pd-catalyzed asymmetric allenylic alkylation between racemic allenyl carbonates and indanone-deriv...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2023-03, Vol.28 (7), p.2927
Hauptverfasser: Xue, Aiqi, Wei, Xingfu, Huang, Yue, Qu, Jingping, Wang, Baomin
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Sprache:eng
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Zusammenfassung:The concurrent construction of 1,3-stereocenters remains a challenge. Herein, we report the development of stereoselective union of a point chiral center with allenyl axial chirality in 1,3-position by Pd-catalyzed asymmetric allenylic alkylation between racemic allenyl carbonates and indanone-derived β-ketoesters. Various target products bearing a broad range of functional groups were afforded in high yield (up to 99%) with excellent enantioselectivities (up to 98% ee) and good diastereoselectivities (up to 13:1 dr).
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28072927