Asymmetric Synthesis of Spirocyclopentane Oxindoles via [2+3] Annulation with 2‐(2‐Oxoindolin‐3‐yl)malononitriles as 1,2‐Carbon Bisnucleophiles
Authors:
- 22 April 2021
- journal article
- research article
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 363 (13) , 3283-3289
Abstract
Carbon bisnucleophiles are important building blocks in organic synthesis and have widespread applications in the construction of carbocyclic compounds. Among them, 1,2‐carbon bisnucleophile has been much less explored. Herein, we developed a [2+3] annulation of 2‐(2‐oxoindolin‐3‐yl)malononitrile with 2‐nitroallylic acetates, where 2‐(2‐oxoindolin‐3‐yl)malononitrile served as a new type of 1,2‐carbon bisnucleophile. Remarkably, the annulation reaction exhibits exclusive chemo‐ and regioselectivity. A Michael addition/SN2 mechanism was proposed to avoid the “anti‐Baldwin” cyclization. This stereoselective strategy provides a facile synthetic route for a new series of spirocyclopentane oxindole derivatives containing three stereogenic centers. magnified imageKeywords
Funding Information
- National Natural Science Foundation of China (81773889, 22001024, 82073998)
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