Asymmetric synthesis of cyclic α-amino acid derivatives by the intramolecular reaction of magnesium carbenoid with an N-magnesio arylamine
| Autor: | Makoto Tadokoro, Tsuyoshi Satoh, Tohru Ohbayashi, Takahito Saitou, Shintaro Mitsunaga, Shimpei Sugiyama |
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| Rok vydání: | 2009 |
| Předmět: |
Intramolecular reaction
Magnesium Stereochemistry Organic Chemistry Enantioselective synthesis chemistry.chemical_element Sulfoxide Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Intramolecular force Nucleophilic substitution Physical and Theoretical Chemistry Carbenoid Pipecolic acid |
| Zdroj: | Tetrahedron: Asymmetry. 20:1697-1708 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2009.06.024 |
| Popis: | The synthesis of pipecolic acid and homopipecolic acid derivatives was developed from ω-(2-aminophenyl)-1-chloroalkyl p -tolyl sulfoxides by treatment with i -PrMgCl. An intramolecular nucleophilic substitution reaction of a magnesium carbenoid with an N -magnesio arylamine is the key step of this reaction. Proline and pipecolic acid derivatives were also synthesized from ω-(arylamino)-1-chloroalkyl p -tolyl sulfoxides by the same chemistry. Starting from enantiomerically pure (1 S , R S )-1-chloro-3-[2-( N -methylamino)phenyl]propyl p -tolyl sulfoxide, enantiomerically pure ( R )-pipecolic acid derivative was obtained. The intramolecular nucleophilic substitution reaction of the magnesium carbenoid with N -magnesio arylamine was proven to take place with inversion of the carbenoid carbon. The stereochemistry of these reactions is also discussed. |
| Databáze: | OpenAIRE |
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