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Dual Catalytic Decarboxylative Allylations of ?-Amino Acids and Their Divergent Mechanisms.

ABSTRACT: The room temperature radical decarboxylative allylation of N-protected ?-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 ?-amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.

SUBMITTER: Lang SB

PROVIDER: S-EPMC4715668 | biostudies-literature | 2015 Dec

REPOSITORIES: biostudies-literature

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Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms.

Lang Simon B SB O'Nele Kathryn M KM Douglas Justin T JT Tunge Jon A JA

Chemistry (Weinheim an der Bergstrasse, Germany) 20151103 51

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. ...[more]

PMID: 26526115

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