Journal
TETRAHEDRON LETTERS
Volume 68, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2021.152909
Keywords
Asymmetric catalysis; Glycidic esters; Cinchona alkaloids; Organic catalysis
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Funding
- Shaanxi Province Key R&D Program Key Industry Innovation Chain Project [2019ZDLSF03-03]
- Key Research and Development Program in Shaanxi Province of China [2019SF-040]
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This study describes a highly enantioselective epoxidation of trans-alpha-cyano-alpha, beta-unsaturated esters using cinchona alkaloid-derived urea and H2O2 as organocatalysts and oxidant, resulting in chiral glycidic ester derivatives with cyano groups in good yields (up to 95%) and excellent enantioselectivities (up to 97% ee). A plausible transition state was proposed for the reaction mechanism.
A highly enantioselective epoxidation of trans-alpha-cyano-alpha, beta-unsaturated esters has been described by using cinchona alkaloid-derived urea and H2O2 as the organocatalysts and oxidant, giving chiral glycidic ester derivatives containing cyano groups in good yields (up to 95%) with excellent enantioselectivities (up to 97% ee). A plausible transition state was also proposed. (C) 2021 Elsevier Ltd. All rights reserved.
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