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Umpolung Approach to Aldol Products via Isoxazoline <i>N</i>-Oxides as Intermediatesстатья
Статья опубликована в высокорейтинговом журнале
Статья опубликована в журнале из списка Web of Science и/или Scopus- Авторы: Ushakov Pavel Yu, Sukhorukov Alexey Yu
- Журнал: Journal of Organic Chemistry
- Том: 89
- Номер: 21
- Год издания: 2024
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Первая страница: 15590
- Последняя страница: 15597
- DOI: 10.1021/acs.joc.4c01671
- Аннотация: A two-step umpolung approach to the diastereoselective synthesis of aldols was developed, in which a conjugated nitroalkene is used as the synthetic equivalent of the enolonium cation, while a sulfur ylide acts as the equivalent of the α-carbinol anion. The resulting isoxazoline N-oxides undergo catalytic reductive cleavage to aldols under mild conditions at room temperature and under 1 atm hydrogen pressure. The efficiency of the method was demonstrated by the synthesis of a series of polysubstituted β-hydroxyketones that are difficult to synthesize using the classical aldol reaction. The developed approach allows for the regiodivergent assembly of aldols by selecting a nitroalkene isomer with the appropriate position of the C,C double bond.
- Добавил в систему: Сухоруков Алексей Юрьевич