4.8 Article

Procedure-Controlled Enantioselectivity Switch in Organocatalytic 2-Oxazolidinone Synthesis

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 33, Pages 12160-12163

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja407027e

Keywords

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Funding

  1. Japanese Ministry of Education, Culture, Sports, Science and Technology
  2. Grants-in-Aid for Scientific Research [25888012, 21106001, 21106005, 23350017] Funding Source: KAKEN

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In a novel organocatalytic formal [3 + 2] cycloaddition to afford chiral 2-oxazolidinones, an enantioselectivity switch could be induced by changing the manner of addition of the reactants, even when the reaction components (cinchona-alkaloid-derived aminothiourea catalyst, substrates, and solvent) were the same.

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