Desymmetrization of Cyclic Sulfonimidamides by Asymmetric Allylation

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Abstract: Herein we report the first transition metal‐catalyzed approach to the enantioenriched synthesis of cyclic sulfonimidamides relying on commercially available palladium catalysts and ligands. High‐throughput experimentation (HTE) was employed to identify the optimal catalyst system and solvent. The method is applied to a variety of saturated and unsaturated rings and exhibits the highest selectivity for 2‐substituted allyl electrophiles. The products are further elaborated to complex, tricyclic scaffolds. DFT experiments presented herein highlight the key ligand substrate interactions leading to the high levels of enantioselectivity.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Desymmetrization of Cyclic Sulfonimidamides by Asymmetric Allylation ; day:12 ; month:07 ; year:2024 ; extent:7
Angewandte Chemie / International edition. International edition ; (12.07.2024) (gesamt 7)

Creator: Gutierrez, David A.
Toth‐Williams, Garrett
Laconsay, Croix J.
Yasuda, Michael
Fettinger, James C.
Di Maso, Michael J.
Shaw, Jared T.

DOI: 10.1002/anie.202407114

URN: urn:nbn:de:101:1-2407121448024.923109667399

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 11:02 AM CEST

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Associated

Gutierrez, David A.
Toth‐Williams, Garrett
Laconsay, Croix J.
Yasuda, Michael
Fettinger, James C.
Di Maso, Michael J.
Shaw, Jared T.

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