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.


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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.

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Publication History

Received: 26 December 2024

Accepted after revision: 05 March 2025

Accepted Manuscript online:
05 March 2025

Article published online:
10 April 2025

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