4.8 Article

Visible-Light Photocatalytic Intramolecular Cyclopropane Ring Expansion

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 27, Pages 7826-7830

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201703334

Keywords

density functional calculations; small ring systems; photocatalysis; reaction mechanisms; ring expansion

Funding

  1. Spanish Government [CTQ2015-64561-R, CTQ2014-59544-P]
  2. European Research Council (ERC-CG) [647550]
  3. UAM
  4. MINECO
  5. ICREA
  6. European Research Council (ERC) [647550] Funding Source: European Research Council (ERC)

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Described herein is a new visible-light photocatalytic strategy for the synthesis of enantioenriched dihydrofurans and cyclopentenes by an intramolecular nitro cyclopropane ring expansion reaction. Mechanistic studies and DFT calculations are used to elucidate the key factors in this new ring expansion reaction, and the need for the nitro group on the cyclopropane.

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