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Synthesis 1989; 1989(6): 439-442
DOI: 10.1055/s-1989-27278
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Diastereoselective Formation of Substituted Cyclic Non-Proteinogenic α-Amino Acids by Cyclization of Activated Imines

Lutz F. Tietze* , Matthias Bratz
  • *Institut für Organische Chemie der Universität Göttingen, Tammannstr. 2, D-3400 Göttingen, Federal Republic of Germany
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Publication Date:
17 September 2002 (online)

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The intramolecular cyclization of alkyl (5-methyl-4-hexenylimino)acetates 7 with trimethylsilyl triflate (TMS-OTf) in toluene or tert-butyl methyl ether affords the cis- and trans-3-isopropenyl-2-piperidinecarboxylates 8 and 9 in ratios from 1:15 to 1:33. TMS-OTf is superior to Lewis acids in this reaction. The imines 7 can be obtained by condensation of 5-methyl-4-hexenylamine 5 and alkyl glyoxylates. Saponification of the diastereomerically pure cyclization product 9 affords the non-proteinogenic α-amino acid 10 (3-isopropenyl-2-piperidinecarboxylic acid).

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