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Asymmetric Synthesis of Spirocyclopentane Oxindoles via [2+3] Annulation with 2‐(2‐Oxoindolin‐3‐yl)malononitriles as 1,2‐Carbon Bisnucleophiles
Author(s) -
Ai YueYan,
Li DongAi,
Li Guo,
Li HePing,
He XiangHong,
Fu XueJu,
Wang YuTing,
Zhan Gu,
Han Bo
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100235
Subject(s) - annulation , oxindole , malononitrile , stereocenter , chemistry , carbon fibers , regioselectivity , michael reaction , stereochemistry , isatin , combinatorial chemistry , organic chemistry , enantioselective synthesis , mathematics , catalysis , algorithm , composite number
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/S N 2 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.