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Dual Catalytic Decarboxylative Allylations of α‐Amino Acids and Their Divergent Mechanisms
Author(s) -
Lang Simon B.,
O'Nele Kathryn M.,
Douglas Justin T.,
Tunge Jon A.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503644
Subject(s) - decarboxylation , chemistry , amino acid , catalysis , dual role , palladium , organic chemistry , combinatorial chemistry , biochemistry
The room temperature radical decarboxylative allylation of N ‐protected α‐amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the α‐amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.