Access to beta-Alkylated beta-Functionalized Ketones via Conjugate Additions to Arylideneisoxazol-5-ones and Mo(CO)(6)-Mediated Reductive Cascade Reactions

Macchia, Antonio; Summa, Francesco F.; Monaco, Guglielmo; Eitzinger, Andreas; Ofial, Armin R.; Di Mola, Antonia und Massa, Antonio (2022): Access to beta-Alkylated beta-Functionalized Ketones via Conjugate Additions to Arylideneisoxazol-5-ones and Mo(CO)(6)-Mediated Reductive Cascade Reactions. In: ACS Omega, Vol. 7, No. 10: pp. 8808-8818

Abstract

1,4-Conjugate addition of ((chloromethyl)sulfonyl)benzenes to arylideneisoxazol-5-ones, followed by one-pot, N-selective trapping in the presence of electrophiles, was investigated. This strategy led to the synthesis of new, stable N-protected isoxazol-5-ones in good yields and high diastereolectivity. The study of the reactivity of obtained products in the presence of the Mo(CO)(6)/H2O system allowed the development of a cascade reaction leading to novel methyl ketones in high yields and unchanged dr bearing an uncommon chloromethinearylsulfonyl end group.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 2470-1343
• Language: English