One-Step Diastereoselective Pyrrolidine Synthesis Using a Sulfinamide Annulating Reagent

One-Step Diastereoselective Pyrrolidine Synthesis Using a Sulfinamide Annulating Reagent

This communication highlights the use of chiral sulfinamides as nitrogen nucleophiles in intermolecular aza-Michael reactions. When chiral sulfinamides are coupled to a chloroethyl group, the corresponding novel annulating reagents can be used to streamline the stereoselective synthesis of complex p...

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Bibliographic Details
Published in:Organic letters Vol. 21; no. 22; pp. 9198 - 9202
Main Authors: Shi, Qing, Greenwood, Nathaniel S, Meehan, Mariah C, Park, Hyunsoo, Galella, Michael, Sandhu, Bhupinder, Khandelwal, Purnima, Coombs, John R, Gallagher, William P, Guerrero, Carlos A, Hynes, John, Dhar, T. G. Murali, Gonzalez Bobes, Francisco, Marcoux, David
Format: Journal Article
Language:English
Published: United States American Chemical Society 15-11-2019
Online Access:Get full text
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Summary:This communication highlights the use of chiral sulfinamides as nitrogen nucleophiles in intermolecular aza-Michael reactions. When chiral sulfinamides are coupled to a chloroethyl group, the corresponding novel annulating reagents can be used to streamline the stereoselective synthesis of complex pyrrolidine-containing molecules. As a result, it has enabled a medicinal chemistry campaign for the synthesis of biologically active RORγt inverse agonists.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03560