4.8 Article

Asymmetric Synthesis of 1,3-Dioxolanes by Organocatalytic Formal [3+2] Cycloaddition via Hemiacetal Intermediates

Journal

ORGANIC LETTERS
Volume 14, Issue 6, Pages 1620-1623

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol3003755

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Funding

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

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A novel asymmetric formal [3 + 2] cycloaddition reaction for the synthesis of 1,3-dioxolanes using cinchona-alkaloid-thiourea-based bifunctional organocatalysts is reported. The reaction proceeds via the formation of hemiacetal intermediates between gamma-hydroxy-alpha,beta-unsaturated ketones and aldehydes.

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