Tetrahedron p. 5789 - 5804 (1998)
Update date:2022-08-04
Topics:
Moeller, Bjoerg
Undheim, Kjell
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 bromoindenes.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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