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Addition of lithiated methoxyallene to aziridines – a novel access to enantiopure piperidine and ß-amino acid derivatives
Vladimir Prisyazhnyuk, Matthias Jachan, Irene Brüdgam, Reinhold Zimmer and Hans-Ulrich Reissig
Jazyk angličtina Země Česko
- MeSH
- alkyny chemická syntéza MeSH
- aziridiny chemická syntéza MeSH
- benzomorfany chemická syntéza MeSH
- lithium MeSH
- organokovové sloučeniny chemická syntéza MeSH
- piperidony chemická syntéza MeSH
Addition of lithiated methoxyallene to aziridine derivatives provided the expected primary addition products. The less substituted carbon of the aziridine ring was attacked selectively. The primary adducts could be converted to enantiopure piperidine derivatives or ß-amino acid derivatives. The unexpected reactions lead to a tricyclic sulfonamide and to alkynyl-substituted aminoethers. The efficient two-step conversion of a piperidone derivative to a benzomorphan demonstrates the potential of this approach to biologically active compounds.
Citace poskytuje Crossref.org
Lit.: 25
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- $a Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, D-14195 Berlin, Germany
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- $a Lit.: 25
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- $a Addition of lithiated methoxyallene to aziridine derivatives provided the expected primary addition products. The less substituted carbon of the aziridine ring was attacked selectively. The primary adducts could be converted to enantiopure piperidine derivatives or ß-amino acid derivatives. The unexpected reactions lead to a tricyclic sulfonamide and to alkynyl-substituted aminoethers. The efficient two-step conversion of a piperidone derivative to a benzomorphan demonstrates the potential of this approach to biologically active compounds.
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