3 years ago

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

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, Jae Kyun Lee, Yong Seo Cho, Seung Young Jung, Sun-Joon Min
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.8b00098

DOI: 10.1021/acs.orglett.8b00098

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