Pd-catalyzed ring restructuring of oxazolidines with alkenes leading to fused polycyclic indolizines
- Author
- Xianjun Xu, Huangdi Feng, Xiaoyong Zhang, Liangliang Song, Luc Van Meervelt, Johan Van der Eycken (UGent) , Jeremy N. Harvey and Erik V. Van der Eycken
- Organization
- Abstract
- A palladium-catalyzed reaction of N-propargyl oxazolidines with alkenes for the synthesis of indolizidines has been developed. Through a sequential 6-exo-dig cyclization/proton transfer/[3+2] cycloaddition/cycloreversion/aromatization process, a series of fused polycyclic indolizines are obtained in moderate to good yields with high functional group tolerance. Experimental and theoretical studies suggest that the [3+2] cycloaddition/cycloreversion of the oxazolidine ring probably involves C-C and C-O bond cleavage, providing a new ring restructuring approach for the synthesis of heterocycles.
- Keywords
- C-C BOND, DIASTEREODIVERGENT SYNTHESIS, DERIVATIVES, ACTIVATION, ANNULATION, PROGRESS, HALIDES, IMINES
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-8758419
- MLA
- Xu, Xianjun, et al. “Pd-Catalyzed Ring Restructuring of Oxazolidines with Alkenes Leading to Fused Polycyclic Indolizines.” ORGANIC LETTERS, vol. 24, no. 5, 2022, pp. 1232–36, doi:10.1021/acs.orglett.2c00007.
- APA
- Xu, X., Feng, H., Zhang, X., Song, L., Van Meervelt, L., Van der Eycken, J., … Van der Eycken, E. V. (2022). Pd-catalyzed ring restructuring of oxazolidines with alkenes leading to fused polycyclic indolizines. ORGANIC LETTERS, 24(5), 1232–1236. https://doi.org/10.1021/acs.orglett.2c00007
- Chicago author-date
- Xu, Xianjun, Huangdi Feng, Xiaoyong Zhang, Liangliang Song, Luc Van Meervelt, Johan Van der Eycken, Jeremy N. Harvey, and Erik V. Van der Eycken. 2022. “Pd-Catalyzed Ring Restructuring of Oxazolidines with Alkenes Leading to Fused Polycyclic Indolizines.” ORGANIC LETTERS 24 (5): 1232–36. https://doi.org/10.1021/acs.orglett.2c00007.
- Chicago author-date (all authors)
- Xu, Xianjun, Huangdi Feng, Xiaoyong Zhang, Liangliang Song, Luc Van Meervelt, Johan Van der Eycken, Jeremy N. Harvey, and Erik V. Van der Eycken. 2022. “Pd-Catalyzed Ring Restructuring of Oxazolidines with Alkenes Leading to Fused Polycyclic Indolizines.” ORGANIC LETTERS 24 (5): 1232–1236. doi:10.1021/acs.orglett.2c00007.
- Vancouver
- 1.Xu X, Feng H, Zhang X, Song L, Van Meervelt L, Van der Eycken J, et al. Pd-catalyzed ring restructuring of oxazolidines with alkenes leading to fused polycyclic indolizines. ORGANIC LETTERS. 2022;24(5):1232–6.
- IEEE
- [1]X. Xu et al., “Pd-catalyzed ring restructuring of oxazolidines with alkenes leading to fused polycyclic indolizines,” ORGANIC LETTERS, vol. 24, no. 5, pp. 1232–1236, 2022.
@article{8758419,
abstract = {{A palladium-catalyzed reaction of N-propargyl oxazolidines with alkenes for the synthesis of indolizidines has been developed. Through a sequential 6-exo-dig cyclization/proton transfer/[3+2] cycloaddition/cycloreversion/aromatization process, a series of fused polycyclic indolizines are obtained in moderate to good yields with high functional group tolerance. Experimental and theoretical studies suggest that the [3+2] cycloaddition/cycloreversion of the oxazolidine ring probably involves C-C and C-O bond cleavage, providing a new ring restructuring approach for the synthesis of heterocycles.}},
author = {{Xu, Xianjun and Feng, Huangdi and Zhang, Xiaoyong and Song, Liangliang and Van Meervelt, Luc and Van der Eycken, Johan and Harvey, Jeremy N. and Van der Eycken, Erik V.}},
issn = {{1523-7060}},
journal = {{ORGANIC LETTERS}},
keywords = {{C-C BOND,DIASTEREODIVERGENT SYNTHESIS,DERIVATIVES,ACTIVATION,ANNULATION,PROGRESS,HALIDES,IMINES}},
language = {{eng}},
number = {{5}},
pages = {{1232--1236}},
title = {{Pd-catalyzed ring restructuring of oxazolidines with alkenes leading to fused polycyclic indolizines}},
url = {{http://doi.org/10.1021/acs.orglett.2c00007}},
volume = {{24}},
year = {{2022}},
}
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