(1R/S,7aS/R)-1-Benzyl-1-[2,8-bis(trifluoromethyl)quinolin-4-yl]-hexahydro-oxazolo[3,4-a]pyridin-3-one-Reference-Cited by-同舟云学术

(1R/S,7aS/R)-1-Benzyl-1-[2,8-bis(trifluoromethyl)quinolin-4-yl]-hexahydro-oxazolo[3,4-a]pyridin-3-one

Published:2023-12-30 Issue:1 Volume:2024 Page:M1756
ISSN:1422-8599
Container-title:Molbank
language:en
Short-container-title:Molbank

Author:

Kucharski Dawid J.¹^ORCID,Boratyński Przemysław J.¹^ORCID

Affiliation:

1. Department of Organic and Medicinal Chemistry, Wrocław University of Technology, Wyspiańskiego 27, 50-370 Wrocław, Poland

Abstract

An unexpected diastereoselective C-alkylation of a mefloquine derivative in up to 57% yield was the result of an attempted Williamson etherification of Boc-mefloquine. The domino reaction involved oxazolidinone ring closure, deprotonation, and stereoselective carbon–carbon bond formation. The structure was confirmed with 2D NMR experiments.

Funder

National Science Center

Publisher

MDPI AG

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

https://www.mdpi.com/1422-8599/2024/1/M1756/pdf

Reference16 articles.

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4. Attrition-Enhanced Deracemization of the Antimalaria Drug Mefloquine;Engwerda;Angew. Chem. Int. Ed.,2019

5. The Reactivity of the N-Boc Protecting Group: An Underrated Feature;Agami;Tetrahedron,2002