Intermolecular Alkyl Radical Additions to Enantiopure N-tert-Butanesulfinyl Aldimines
| Autor: | M. Carmen Maestro, Inés Alonso, M. Mercedes Rodriguez‐Fernandez, José A. Fernández-Salas, José L. García-Ruano |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
chemistry.chemical_classification
Aldimine Molecular Structure Radical Aryl Organic Chemistry Sulfonium Compounds Stereoisomerism Biochemistry Medicinal chemistry chemistry.chemical_compound Enantiopure drug chemistry Alkanes Organic chemistry Stereoselectivity Imines Amines Physical and Theoretical Chemistry Alkyl |
| Zdroj: | Organic Letters. 15:1658-1661 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol400439g |
| Popis: | The sulfinyl group in (R)-N-tert-butanesulfinyl aldimines provides efficient control of the stereoselectivity in the intermolecular reactions with alkyl radicals. The methodology is applicable to aryl, heteroaryl, benzyl, and alkynyl imines, even those containing CN, CO2Me, COR, and OH groups. The best results are attained with hindered radicals (tertiary and secondary ones) without C═N bond reduction. This reaction complements the well-established organometallic additions to N-sulfinyl aldimines to obtain enantiomerically pure functionalized α-branched primary amines. |
| Databáze: | OpenAIRE |
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