A1 Refereed original research article in a scientific journal

Switchable Access to Different Spirocyclopentane Oxindoles by N-Heterocyclic Carbene Catalyzed Reactions of Isatin-Derived Enals and N-Sulfonyl Ketimines




AuthorsWang L, Li S, Blumel M, Puttreddy R, Peuronen A, Rissanen K, Enders D

PublisherWILEY-V C H VERLAG GMBH

Publication year2017

JournalAngewandte Chemie International Edition

Journal name in sourceANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Journal acronymANGEW CHEM INT EDIT

Volume56

Issue29

First page 8516

Last page8521

Number of pages6

ISSN1433-7851

DOIhttps://doi.org/10.1002/anie.201704210(external)


Abstract
A novel NHC-catalyzed annulation protocol for the asymmetric synthesis of biologically important beta-lactam fused spirocyclopentane oxindoles with four contiguous stereocenters, including two quaternary carbon centers, was developed. Alternatively, spirocyclopentane oxindoles containing an enaminone moiety can be achieved using the same starting materials, isatin-derived enals, and N-sulfonyl ketimines, in the presence of a slightly different NHC catalytic system. This switchable annulation strategy enables the selective assembly of both heterocyclic scaffolds with good yields and excellent enantioselectivities for a broad range of substrates.



Last updated on 2024-26-11 at 14:46