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Recent advances in ring-opening of donor acceptor cyclopropanes using C-nucleophiles

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ORGANIC & BIOMOLECULAR CHEMISTRY
卷 19, 期 5, 页码 965-982

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob02437f

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  1. CSIR, India [02(0326)/17/EMR-II]
  2. Presidency University (FRPDF grant)

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Ring-opening transformations of donor-acceptor cyclopropanes (DAC) with carbon-centered nucleophiles have shown remarkable progress in the synthesis of diverse 1,3-bifunctional compounds, leading to successful multistep synthesis of complex target molecules in recent years.
Ring-opening transformations of donor-acceptor cyclopropanes (DAC) with carbon-centered nucleophiles is a simple, straight-forward approach to 1,3-bifunctional compounds that has witnessed remarkable progress over the past several years. To date, different reactivity patterns of DACs have been successfully exploited in racemic/stereoselective syntheses of various acyclic compounds or carbocycles with an impressive structural diversity. The thriving strategies have been successfully utilized in multistep synthesis of complex target molecules. Herein, the recent advances (2015-present) in the ring-opening of DAC involving electron rich arenes and indoles, active methylene compounds, various dipolarophiles, organoborates/boronates, vinyl ethers etc. following Friedel-Crafts alkylation, annulation/formal cycloaddition reaction, organocatalytic reaction, Nazarov cyclisation etc. are presented.

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