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Umpolung Strategy for the One-Pot Synthesis of Highly Steric Bispirooxindoles via the l-Amino Acid Ester-Promoted In Situ Reduction/Nucleophilic Addition/Cyclization Cascade Reaction.

Authors :
Ren JW
Zhang HX
Han CS
Zhang QH
Di RD
Sun JH
Source :
The Journal of organic chemistry [J Org Chem] 2024 Sep 06; Vol. 89 (17), pp. 12716-12724. Date of Electronic Publication: 2024 Aug 13.
Publication Year :
2024

Abstract

On the basis of a novel umpolung strategy, an efficient l-amino acid ester-mediated in situ reduction of 2-(2-oxoindolin-3-ylidene)malononitrile and sequential nucleophilic addition/cyclization cascade reaction is reported. Various densely substituted cyclopentene bispirooxindoles and dihydrofuran bispirooxindoles with two quaternary spirocenters were constructed in high yields (≤93%) with excellent diastereoselectivities (>20:1 dr). The method has advantages of readily available starting materials, mild reaction conditions, a one-pot process, a metal-free biomimetic reducing agent, a wide substrate scope, and operational simplicity (single filtration without column chromatography).

Details

Language :
English
ISSN :
1520-6904
Volume :
89
Issue :
17
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
39138971
Full Text :
https://doi.org/10.1021/acs.joc.4c00965