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Synlett 2000; 2000(12): 1729-1732
DOI: 10.1055/s-2000-8683
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Titanium-Mediated Diastereoselective Formation of (Z)-1-(1-Alkenyl)-2-substituted-cyclopropyl Esters Efficient Precursors of (Z)-2,3-Methanoamino Acids

Sandrine Racouchot* , Jean Ollivier, J. Salaün
  • *Laboratoire des Carbocycles (Associé au CNRS), Institut de Chimie Moléculaire d'Orsay, Bât. 420, Université de Paris-Sud, 91405 ORSAY, France; Fax +33(1)69 15 62 78; E-mail: jasalaun@icmo.u-psud.fr
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Publication Date:
31 December 2000 (online)

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The titanium-mediated cyclopropanation of homoallyl alk-2-enoates, emerged as the most convenient method to form diastereomerically pure (Z)-1-(1-alkenyl)-2-alkylcyclopropanols, precursors of significant 1,1-dimethyleneallylmetal species. Then, azidation of such complexes followed by a simple reduction-oxidation sequence provided diastereochemically pure (Z)-2,3-methanoamino acids.

titanacyclopropane - (Z)-1-(1-alkenyl)-2-alkylcyclopropyl esters - π-1,1-dimethyleneallylpalladium complexes - azidation - (Z)-2,3-methanoamino acids