Highly Diastereoselective Three-Component Vinylogous Mannich Reaction between Isoquinolines, Acyl/Sulfonyl Chlorides, and Silyloxyfurans
| Autor: | Robert H. Dodd, Pascal Retailleau, Philippe Hermange, Marie Elise Tran Huu Dau |
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| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Rok vydání: | 2009 |
| Předmět: |
Models
Molecular Sulfonyl chemistry.chemical_classification Chiral auxiliary 010405 organic chemistry Component (thermodynamics) Organic Chemistry Stereoisomerism [SDV.BC]Life Sciences [q-bio]/Cellular Biology Isoquinolines Sulfinic Acids 010402 general chemistry 01 natural sciences Biochemistry Sulfonyl chloride Medicinal chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Isomerism chemistry Yield (chemistry) Physical and Theoretical Chemistry Isoquinoline Mannich reaction |
| Zdroj: | Organic Letters Organic Letters, American Chemical Society, 2009, 11 (18), pp.4044-7. ⟨10.1021/ol901452d⟩ |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol901452d |
| Popis: | International audience; Reaction of an isoquinoline, a silyloxyfuran, and an acyl or sulfonyl chloride provides easy access to a wide variety of isoquinolinobutyrolactones with excellent yields and diastereoselectivites (R*,R* isomer), even in the case of formation of quaternary centers (i.e., R(3) or R(4) = Me). Moreover, the use of a chiral auxiliary allowed formation of a single stereoisomer in 96% yield. This represents the first examples of asymmetric vinylogous Mannich reactions on isoquinolinium salts. |
| Databáze: | OpenAIRE |
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