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Palladium‐Catalyzed Cyclization Reactions of Acetylene‐Containing Amino Acids
Author(s) -
Wolf Larissa B.,
Tjen Kim C. M. F.,
ten Brink Hefziba T.,
Blaauw Richard H.,
Hiemstra Henk,
Schoemaker Hans E.,
Rutjes Floris P. J. T.
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200201)344:1<70::aid-adsc70>3.0.co;2-1
Subject(s) - chemistry , acetylene , palladium , amino acid , catalysis , amine gas treating , organic chemistry , carboxylate , nitrogen , biochemistry
Enantiomerically pure acetylene‐containing α‐amino acids were used as versatile starting materials for the synthesis of a variety of heterocycles via Pd‐mediated cyclization reactions. Depending on the protecting group strategy, both the carboxylate and the amine function of the amino acids could participate in the cyclizations, thus giving rise to oxygen heterocycles (α‐aminolactones) and nitrogen heterocycles (cyclic α‐amino acid derivatives), respectively. Beside the straightforward cyclization, cyclization/cross‐coupling reactions were also successfully carried out to provide the corresponding substituted cyclic amino acid derivatives.