Umpolung Approach to Aldol Products via Isoxazoline N-Oxides as Intermediates

Umpolung Approach to Aldol Products via Isoxazoline N-Oxides as Intermediates Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2024, Volume: 89, Number: 21, Pages: 15590–15597 Pages count : DOI: 10.1021/acs.joc.4c01671

Authors

Ushakov Pavel Yu. ¹ , Sukhorukov Alexey Yu. ¹

Affiliations

1	Laboratory of Organic and Metal−Organic Nitrogen−Oxygen Systems, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect, 47, Moscow 119991, Russian Federation

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.

Ushakov P.Y. , Sukhorukov A.Y.
Umpolung Approach to Aldol Products via Isoxazoline N-Oxides as Intermediates
Journal of Organic Chemistry. 2024. V.89. N21. P.15590–15597. DOI: 10.1021/acs.joc.4c01671 WOS Scopus OpenAlex

Web of science:	WOS:001338303700001
Scopus:	2-s2.0-85206645957
OpenAlex:	W4403327545

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