Selective azetidine and tetrahydropyridine formation via Pd-catalyzed cyclizations of allene-substituted amines and amino acids.
[reaction: see text] By choosing the right substituents either highly functionalized unusual four-membered ring amino acids or the isomeric pipecolic acid derivatives are obtained in enantiomerically pure form. Starting material is a linear allene-containing amino acid that has been resolved via biocatalysis.
Rutjes
F P
FP
Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands. florisr@org.chem.uva.nl
Tjen
K C
KC
Wolf
L B
LB
Karstens
W F
WF
Schoemaker
H E
HE
Hiemstra
H
H