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Zhang XZ, Deng YH, Gan KJ, et al. Tandem Spirocyclopropanation/Rearrangement Reaction of Vinyl p-Quinone Methides with Sulfonium Salts: Synthesis of Spirocyclopentenyl p-Dienones. Org Lett. 2017;19(7):1752-1755doi: 10.1021/acs.orglett.7b00516.
Zhang, X. Z., Deng, Y. H., Gan, K. J., Yan, X., Yu, K. Y., Wang, F. X., & Fan, C. A. (2017). Tandem Spirocyclopropanation/Rearrangement Reaction of Vinyl p-Quinone Methides with Sulfonium Salts: Synthesis of Spirocyclopentenyl p-Dienones. Organic letters, 19(7), 1752-1755. https://doi.org/10.1021/acs.orglett.7b00516
Zhang, Xiang-Zhi, et al. "Tandem Spirocyclopropanation/Rearrangement Reaction of Vinyl p-Quinone Methides with Sulfonium Salts: Synthesis of Spirocyclopentenyl p-Dienones." Organic letters vol. 19,7 (2017): 1752-1755. doi: https://doi.org/10.1021/acs.orglett.7b00516
Zhang XZ, Deng YH, Gan KJ, Yan X, Yu KY, Wang FX, Fan CA. Tandem Spirocyclopropanation/Rearrangement Reaction of Vinyl p-Quinone Methides with Sulfonium Salts: Synthesis of Spirocyclopentenyl p-Dienones. Org Lett. 2017 Apr 07;19(7):1752-1755. doi: 10.1021/acs.orglett.7b00516. Epub 2017 Mar 24. PMID: 28339217.
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Org Lett. 2017 Apr 07;19(7):1752-1755. doi: 10.1021/acs.orglett.7b00516. Epub 2017 Mar 24.

Tandem Spirocyclopropanation/Rearrangement Reaction of Vinyl p-Quinone Methides with Sulfonium Salts: Synthesis of Spirocyclopentenyl p-Dienones.

Organic letters

Xiang-Zhi Zhang, Yu-Hua Deng, Kang-Ji Gan, Xu Yan, Ke-Yin Yu, Fang-Xin Wang, Chun-An Fan

Affiliations

  1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , 222 Tianshui Nanlu, Lanzhou 730000, China.
  2. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences , Lanzhou 730000, China.
  3. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300071, China.

PMID: 28339217 DOI: 10.1021/acs.orglett.7b00516

Abstract

A novel base-mediated tandem spirocyclopropanation/rearrangement reaction of vinyl p-quinone methides (p-VQMs) with sulfonium salts is described. The unprecedented reactivity of p-VQMs was explored for the first time in the spiroannulation cascade, providing a stereoselective approach to the construction of synthetically interesting, densely functionalized spirocyclopentenyl p-dienones.

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