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Synlett 1991; 1991(2): 87-89
DOI: 10.1055/s-1991-20635
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C-Alkylation of Functionally Substituted Carbanions with Cyclopropiminium Ions: A New Route to Cyclopropane Amino Acids1

Ansgar Mertin* , Thies Thiemann, Ian Hanss, Armin de Meijere
  • *Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-2000 Hamburg 13, Germany
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Publication Date:
07 March 2002 (online)

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1-Diallylamino- and 1-dibenzylamino-1-cyclopropanols (3a,b) can easily be prepared in high yield from the corresponding secondary amines and cyclopropanone hemiacetal 1 (1-ethoxy-1-cyclopropanol). Their reactions with functionalized carbon nucleophiles such as ketene silyl acetals (1-methoxy-1-trimethylsiloxyethylene and methyl 3-methoxy-3-trimethylsiloxy-2-propenoate) and lithium enolates of alkyl esters under titanium(IV) chloride catalysis yield protected cyclopropane amino esters [1-aminocyclopropaneacetic acid derivatives]; subsequent deprotection to the free amino acids is also exemplified.