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Synlett 1992; 1992(9): 735-737
DOI: 10.1055/s-1992-21473
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A New Versatile Synthesis of tert-Butyl 2-Alkoxycyclopropanecarboxylates1

Hans Henniges* , Hans-Christian Militzer, Armin de Meijere
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, D-3400 Göttingen, Germany
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Publication Date:
08 March 2002 (online)

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Bromination of alkyl vinyl ethers 1 and subsequent reaction of the resulting dibromides 2 with tert-butyl lithioacetate leads to tert-butyl 3-alkoxy-4-bromobutanoates 3 in good to very good yields. By treatment of 3 with bases such as potassium tert-butoxide, lithium diisopropylamide and lithium hexamethyldisilazide, it can be transformed in high yields and very good E/Z-diastereoselectivity to tert-butyl (E/Z)-2-alkoxycyclopropanecarboxylates 4. This two step synthesis of 4 represents a simple and safe alternative to existing methods using diazo compounds.

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