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

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

doi:10.1021/acs.orglett.8b00098

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.

Authors

Hanbyeol Jo¹, Ahmed H E Hassan², Seung Young Jung^{3

4}, Jae Kyun Lee³, Yong Seo Cho³, Sun-Joon Min¹

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.

Publication types

Research Support, Non-U.S. Gov't