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Jo H, Hassan AHE, Jung SY, et al. Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions of N-Aryl Pyrrolidines. Org Lett. 2018;20(4):1175-1178doi: 10.1021/acs.orglett.8b00098.
Jo, H., Hassan, A. H. E., Jung, S. Y., Lee, J. K., Cho, Y. S., & Min, S. J. (2018). Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions of N-Aryl Pyrrolidines. Organic letters, 20(4), 1175-1178. https://doi.org/10.1021/acs.orglett.8b00098
Jo, Hanbyeol, et al. "Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions of N-Aryl Pyrrolidines." Organic letters vol. 20,4 (2018): 1175-1178. doi: https://doi.org/10.1021/acs.orglett.8b00098
Jo H, Hassan AHE, Jung SY, Lee JK, Cho YS, Min SJ. Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions of N-Aryl Pyrrolidines. Org Lett. 2018 Feb 16;20(4):1175-1178. doi: 10.1021/acs.orglett.8b00098. Epub 2018 Jan 30. PMID: 29381368.
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Org Lett. 2018 Feb 16;20(4):1175-1178. doi: 10.1021/acs.orglett.8b00098. Epub 2018 Jan 30.

Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions of N-Aryl Pyrrolidines.

Organic letters

Hanbyeol Jo, Ahmed H E Hassan, Seung Young Jung, Jae Kyun Lee, Yong Seo Cho, Sun-Joon Min

Affiliations

  1. Department of Chemical & Molecular Engineering/Applied Chemistry, Hanyang University , Ansan, Gyeonggi-do 15588, Republic of Korea.
  2. Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University , Mansoura 35516, Egypt.
  3. Center for Neuro-Medicine, Korea Institute of Science and Technology (KIST) , Seoul, 02792, Republic of Korea.
  4. Department of Chemistry, Korea University , Seoul 02841, Republic of Korea.

PMID: 29381368 DOI: 10.1021/acs.orglett.8b00098

Abstract

A concise synthesis of 8-azabicyclo[3.2.1]octanes via sequential oxidative Mannich reactions is described. This approach involves an intermolecular oxidative Mannich coupling reaction between N-aryl pyrrolidines with TMS enol ether and a subsequent intramolecular oxidative Mannich cyclization of the corresponding silyl enol ether. DDQ is used as a key oxidant for both reactions.

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