AI Article Synopsis
- A new rhodium-catalyzed method is introduced for carbene N-H insertion that effectively controls both C-N axial and spiro-central chiralities, leading to the creation of enantiopure -arylindolinone-spiroacetal derivatives.
- This strategy showcases high yields and excellent enantioselectivities, offering potential for functional group tolerance and late-stage diversification in chemical synthesis.
- Density Functional Theory (DFT) calculations suggest that the N-H insertion is pivotal for determining axial chirality, while a 1,5-hydrogen shift is specifically influenced by the spirocycle structure.
Article Abstract
A rhodium-catalyzed carbene N-H insertion protocol for simultaneously controlling the C-N axial and spiro-central chiralities is disclosed, resulting in the rapid assembly of enantiopure -arylindolinone-spiroacetal derivatives in high yields with excellent enantioselectivities. This promising strategy features the chiral C-N axis, spiro-central chirality, functional group tolerance, and late-stage diversification. DFT calculations indicate that the N-H insertion is the axial-chirality-determining step and that the 1,5-H shift step is regiospecifically caused by the spirocycle.
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| http://dx.doi.org/10.1021/acs.orglett.3c03163 | DOI Listing |
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