Abstract
Stereoselective syntheses of cyclic α-amino acids are described. The α-carbon of the amino acid is incorporated into a five- or six-membered vicinal dimethylenecycloalkane or conjugated methylenecycloalkene. Palladium-catalysis was used for cycloisomerization of intermediate enynes and intramolecular Heck type cyclizations of bromodienes. A stereoselective elimination from a homoallylic Pd-intermediate is described. Enantiomerically pure substrates for the cyclization reactions were available by stepwise alkylations of the chiral auxiliary ( R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine with bromo-alkenes and -alkynes.
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