Synthesis of 2-azabicyclo[2.1.0]pentanes by the intramolecular nucleophilic substitution of cyclopropylmagnesium carbenoids with magnesium anilide
| Autor: | Tsutomu Kimura, Toshiki Nishimura, Tsuyoshi Satoh, Natsumi Wada |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Chiral auxiliary 010405 organic chemistry Stereochemistry Carboxylic acid Organic Chemistry Sulfoxide Pentanes 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Deprotonation chemistry Intramolecular force Drug Discovery Nucleophilic substitution Moiety |
| Zdroj: | Tetrahedron. 73:2623-2628 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2017.03.045 |
| Popis: | A variety of 2-azabicyclo[2.1.0]pentanes were synthesized by the intramolecular nucleophilic substitution of cyclopropylmagnesium carbenoids with magnesium anilide. The 1-chlorocyclopropyl p -tolyl sulfoxides possessing an N -aryl-substituted aminomethyl group were prepared from dichloromethyl p -tolyl sulfoxide, α,β-unsaturated carboxylic acid esters, and anilines in four steps. The deprotonation of the amine with t -BuMgCl followed by sulfoxide/magnesium exchange of the sulfoxides with i -PrMgCl led to the generation of the cyclopropylmagnesium carbenoids possessing a magnesium anilide moiety. Subsequent intramolecular nucleophilic substitution of the cyclopropylmagnesium carbenoids occurred in a 4-exo-tet manner to give the 2-azabicyclo[2.1.0]pentanes. The optically active 2-azabicyclo[2.1.0]pentane was synthesized using a p -tolylsulfinyl group as a chiral auxiliary. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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