Diastereodivergent aminocatalyzed spirocyclization strategies using 4-alkylideneisoxazol-5-ones and methyl vinyl ketones

Author(s)

da Silva, Amanda F. ^[1] ; Leonarczyk, Ives A. ^[2] ; Ferreira, Marco A. B. ^[2] ; Jurberg, Igor D. ^[1]

Affiliation

^[1] Univ Estadual Campinas, Inst Chem, BR-13083862 Campinas, SP - Brazil

^[2] Univ Fed Sao Carlos, Ctr Excellence Res Sustainable Chem CERSusChem, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: ORGANIC CHEMISTRY FRONTIERS; v. 7, n. 22, p. 3599-3607, NOV 21 2020.
• Web of Science Citations: 0

Abstract

Diasterodivergent aminocatalyzed approaches have been developed for the synthesis of racemic 6,10-cis-spiroisoxazol-5-ones and highly enantioenriched 6,10-trans-spiroisoxazol-5-ones, both protocols starting from 4-alkylideneisoxazol-5-ones and methyl vinyl ketones. Reaction monitoring by H-1 NMR and HRMS, and DFT calculations have been performed in order to support a mechanistic rationale explaining such outcomes, depending on the reaction conditions employed. (AU)

• FAPESP's process: 15/08541-6 - Nuclear magnetic resonance spectroscopy: beyond molecular structure assignment
• Grantee: Claudio Francisco Tormena
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 17/24017-0 - Application of Isoxazolones in Organic Synthesis
• Grantee: Igor Dias Jurberg
• Support Opportunities: Regular Research Grants
• FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Grants - Research Centers in Engineering Program