Rh(II)-Catalyzed Enantioselective S -Alkylation of Sulfenamides with Acceptor-Acceptor Diazo Compounds Enables the Synthesis of Sulfoximines Displaying Diverse Functionality.
| Autor: | Patel S; Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States., Greenwood NS; Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States., Mercado BQ; Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States., Ellman JA; Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States. |
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| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2024 Jul 26; Vol. 26 (29), pp. 6295-6300. Date of Electronic Publication: 2024 Jul 14. |
| DOI: | 10.1021/acs.orglett.4c02402 |
| Abstrakt: | The Rh(II)-catalyzed enantioselective S -alkylation of sulfenamides with α-amide diazoacetates at 1 mol % catalyst loading to obtain sulfilimines in high yields and enantiomeric ratios of up to 99:1 is reported. The enantioenriched sulfilimine products incorporate versatile amide functionality poised for further elaboration to diverse sulfoximines with multiple stereogenic centers, including by highly diastereoselective sulfilimine and sulfoximine α-alkylation with alkylating agents and epoxides and by interconversion of the amide to N - tert -butanesulfinyl aldimines, followed by diastereoselective additions. |
| Databáze: | MEDLINE |
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