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Continuous and convergent access to vicinyl amino alcohols

MPG-Autoren
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Nobuta,  Tomoya
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Xiao,  Guozhi
Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Ghislieri,  Diego
Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Gilmore,  Kerry
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Zitation

Nobuta, T., Xiao, G., Ghislieri, D., Gilmore, K., Seeberger, P. H., & Seeberger, P. H. (2015). Continuous and convergent access to vicinyl amino alcohols. Chemical Communications, 51, 15133-15136. doi:10.1039/C5CC06093A.


Zitierlink: https://hdl.handle.net/11858/00-001M-0000-0028-4B47-3
Zusammenfassung
Five active pharmaceutical ingredients (APIs) containing the vicinyl amino alcohol moiety were synthesized using a convergent chemical assembly system. The continuous system is composed of four flow reaction modules: biphasic oxidation, Corey-Chaykovsky epoxidation, phenol alkylation, and epoxide aminolysis. Judicious choice of reagents and module order allowed for two classes of [small beta]-amino alcohols, aryl and aryloxy, to be synthesized in good (27-69%) overall yields.