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Cheng YF, Rong HJ, Yi CB, et al. Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines. Org Lett. 2015;17(19):4758-61doi: 10.1021/acs.orglett.5b02298.
Cheng, Y. F., Rong, H. J., Yi, C. B., Yao, J. J., & Qu, J. (2015). Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines. Organic letters, 17(19), 4758-61. https://doi.org/10.1021/acs.orglett.5b02298
Cheng, Yong-Feng, et al. "Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines." Organic letters vol. 17,19 (2015): 4758-61. doi: https://doi.org/10.1021/acs.orglett.5b02298
Cheng YF, Rong HJ, Yi CB, Yao JJ, Qu J. Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines. Org Lett. 2015 Oct 02;17(19):4758-61. doi: 10.1021/acs.orglett.5b02298. PMID: 26378343.
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Org Lett. 2015 Oct 02;17(19):4758-61. doi: 10.1021/acs.orglett.5b02298.

Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines.

Organic letters

Yong-Feng Cheng, Hao-Jie Rong, Cheng-Bo Yi, Jun-Jun Yao, Jin Qu

Affiliations

  1. State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University , Tianjin 300071, China.

PMID: 26378343 DOI: 10.1021/acs.orglett.5b02298

Abstract

By using o-benzoquinone as an internal oxidant, the regio- and diastereoselective functionalization of the secondary over the tertiary α-C-H bond of 2-substituted pyrrolidines is first realized. Subsequent intermolecular addition of a nucleophile to the generated N,O-acetal and cleavage of the aromatic substituent leads to 2,5-disubstituted pyrrolidines.

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