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Reaction of magnesium cyclopropylidene with N-lithio arylamines: a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles |
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| Authors: | Tsuyoshi Satoh Mariko Miura Yoshimi Yokoyama |
| Institution: | a Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan b Department of Chemistry, Faculty of Science, Kyushu University, Hakozaki 6-10-1, Higashi-ku, Fukuoka 812-8581, Japan |
| Abstract: | Magnesium cyclopropylidene was generated from 1-chlorocyclopropyl phenyl sulfoxide with i-PrMgCl in THF at −78 °C in high yield by a sulfoxide-magnesium exchange reaction. The generated magnesium cyclopropylidene was found to be reactive with N-lithio arylamines to give α-amino-substituted cyclopropylmagnesiums. The reaction of the α-amino-substituted cyclopropylmagnesiums with several electrophiles was examined and a new method for a synthesis of cyclopropane amino acid derivatives was realized. |
| Keywords: | Sulfoxide Sulfoxide-magnesium exchange Magnesium cyclopropylidene α-Amino-substituted cyclopropylmagnesium Cyclopropane amino acid |
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