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Synthesis 2023; 55(03): 499-509
DOI: 10.1055/a-1915-7794
DOI: 10.1055/a-1915-7794
paper
Stereospecific Synthesis of Substituted Sulfamidates as Privileged Morpholine Building Blocks
This work was supported by the Swiss National Science Foundation (Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung; grants 310030_153211, 316030_133860, 316030_198526 and 200021_204602); a Swiss Cancer Research Foundation grant (KFS-5442-08-2021) and a Stiftung für Krebsbekämpfung (grant 341; to M.P.W.).
Abstract
Morpholine is a heterocyclic moiety that is widely used in medicinal chemistry as a building block. It has unique physicochemical properties, as it can improve both pharmacokinetic and pharmacodynamic properties of active pharmaceutical ingredients. However, the efficient synthesis of enantiomerically pure morpholine building blocks remains challenging. Herein, we report the synthesis of optically pure 3-hydroxymethylmorpholine building blocks, as well as their sulfamidates, exploiting a stereospecific strategy from chiral pool material.
Key words
morpholines - sulfamidates - stereoselectivity - chiral building blocks - privileged scaffoldsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1915-7794.
- Supporting Information
Publication History
Received: 22 June 2022
Accepted after revision: 02 August 2022
Accepted Manuscript online:
02 August 2022
Article published online:
10 October 2022
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