Abstract
The new 1,1-dimethylpropargylamine surrogates, 1-ethynylcyclopropylamine
(3 ) and 1-ethynylcyclobutylamine (5 ), were prepared as hydrochlorides from
cyclopropylacetylene and 6-chlorohex-1-yne in overall yields of
39 and 25%, respectively, on a scale of up to 300 mmol.
The amine 3 was converted into the new
ethynyl-extended 1-aminocyclopropanecarboxylic acid 4 ,
and both the amine 3 as well as the amino
acid 4 were made available as their N -Fmoc-protected derivatives.
Key words
alkynes - amines - amino acids - Curtius
degradation - small rings
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