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Synlett 1992; 1992(6): 505-506
DOI: 10.1055/s-1992-21395
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Efficient Synthesis of a Novel GABA Analogue Incorporating a Cyclopropene Ring

Klaus Paulini* , H. -U. Reissig
  • *Institut füur Organische Chemie der Technischen Hochschule Darmstadt, Petersenstrasse 22, D-6100 Darmstadt, Germany
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Publication Date:
08 March 2002 (online)

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N,N-Bis(trimethylsilyl)-2-propynylamine (1) was smoothly transformed into alkyl 2-cyclopropenecarboxylates 2 and 3 by alkyl diazoacetates under rhodium(II) acetate dimer catalysis. The corresponding γ-amino acid 7 (2-aminomethyl-2-cyclopropene-carboxylic acid) was prepared in good yield from 3 via 5 and 6 by desilylation, ester cleavage under acidic conditions, and neutralization. Diels-Alder reaction of cyclopropene derivative 2 with cyclopentadiene selectively provided methyl 2-[bis(trimethylsilyl)aminomethyl]tricyclo[3.2.1.02,4]oct-6-ene-3-carboxylate (8).

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