Synlett 2025; 36(11): 1524-1529
DOI: 10.1055/a-2551-4541
letter

Chiral Silver Alkoxide Catalyzed Asymmetric Mannich-Type Reaction of Alkenyl Esters with Isatin Imines

Akira Yanagisawa
,
Kyonosuke Gomi
,
Ririko Uga
,
Ryusei Suga

This work was supported by MEXT/JSPS KAKENHI (Grant Numbers 16K05766 and 19K05450). We gratefully acknowledge the financial support from Nippon Chemical Industrial Co., Ltd.


Preview

Abstract

A catalytic enantioselective Mannich-type reaction of alkenyl esters with isatin imines was achieved by using a Tol-BINAP·AgSbF6 complex as the chiral precatalyst and N,N-diisopropylethylamine as the base precatalyst in the presence of methanol. Optically active 3-alkylated 3-amino-2-oxindoles having up to 98% ee were diastereoselectively obtained in moderate to high yields not only from acyclic alkenyl esters but also from cyclic esters through the in situ generated chiral silver enolates.

Supporting Information



Publikationsverlauf

Eingereicht: 26. Dezember 2024

Angenommen nach Revision: 05. März 2025

Accepted Manuscript online:
05. März 2025

Artikel online veröffentlicht:
10. April 2025

© 2025. Thieme. All rights reserved

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany