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Halogenated Allyl Alcohol Derivatives ‐ Versatile Electrophiles for Palladium‐Catalyzed Allylic Alkylations
Author(s) -
Kohr Michael,
Kazmaier Uli
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900310
Subject(s) - chemistry , allylic rearrangement , electrophile , moiety , halogenation , palladium , catalysis , alkylation , allyl alcohol , combinatorial chemistry , tsuji–trost reaction , organic chemistry
Brominated and iodinated allylic substrates can be subjected to palladium‐catalyzed allylic alkylation of amino acid and peptide ester enolates. The incorporation of a vinylic halide functionality into the allylic substrate allows a direct modification of the allylated peptide via cross coupling chemistry. Therefore, the direct introduction of a vinylhalide side chain into a peptide is an interesting alternative to the stannylallylation/halogenation approach. However, the haloallylation is not as trivial as normal allylic alkylations, because the incorporation of a second, competitive electrophilic center into the allyl moiety requires careful optimization of the reaction conditions.