Formal Nucleophilic Substitution of Bromocyclopropanes with Amides en route to Conformationally Constrained β-Amino Acid Derivatives

Formal Nucleophilic Substitution of Bromocyclopropanes with Amides en route to Conformationally Constrained β-Amino Acid Derivatives

A chemo- and diastereoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides with secondary amides is described. This method allows for convergent and highly selective synthesis of trans-β-aminocyclopropane carboxylic acid derivatives.

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Veröffentlicht in:Organic letters 2010-09, Vol.12 (18), p.3968-3971
Hauptverfasser: Prosser, Anthony R, Banning, Joseph E, Rubina, Marina, Rubin, Michael
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Amino Acids - chemistry
Bromine Compounds - chemistry
Cyclopropanes - chemistry
Models, Molecular
Molecular Conformation
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Beschreibung
Zusammenfassung:A chemo- and diastereoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides with secondary amides is described. This method allows for convergent and highly selective synthesis of trans-β-aminocyclopropane carboxylic acid derivatives.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101228k