Synthesis of Cyclic β-Amino Acid Derivatives by Desymmetrization and Lossen Rearrangement of N -Sulfoxy Meso-Succinimides.
| Autor: | Hardee D; Department of Chemistry, UNC College of Arts and Sciences, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States., Huh CW; The University of Kansas Chemical Methodologies and Library Development Center, 2034 Becker Dr., Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, United States., Aubé J; Department of Chemistry, UNC College of Arts and Sciences, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States.; The University of Kansas Chemical Methodologies and Library Development Center, 2034 Becker Dr., Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, United States.; Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States. |
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| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2024 Jul 05; Vol. 89 (13), pp. 9420-9426. Date of Electronic Publication: 2024 Jun 19. |
| DOI: | 10.1021/acs.joc.4c00701 |
| Abstrakt: | Bifunctional thiourea-based organocatalysts facilitate an enantioselective desymmetrization and Lossen rearrangement cascade reaction of N -sulfoxy meso -succinimides, resulting in the synthesis of cyclic β-amino acid derivatives. This catalytic system was optimized for bicyclic and tricyclic succinimide substrates affording yields from 61-91% and up to 96:4 er. This reaction proceeds via the group selective addition of the primary alcohol nucleophile to an enantiotopic carbonyl group with sequential rearrangement of the intermediate O -sulfonyl hydroxamate ester. |
| Databáze: | MEDLINE |
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