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Organocatalysts Derived from Unnatural α‐Amino Acids: Scope and Applications
Author(s) -
Agirre Maddalen,
Arrieta Ana,
Arrastia Iosune,
Cossío Fernando P.
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801296
Subject(s) - iminium , amino acid , chemistry , organocatalysis , proline , enamine , stereoselectivity , alanine , bicyclic molecule , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , enantioselective synthesis , biochemistry
The organocatalytic properties of unnatural α‐amino acids are reviewed. Post‐translational derivatives of natural α‐amino acids include 4‐hydroxy‐ l ‐proline and 4‐amino‐ l ‐proline scaffolds, and also proline homologues. The activity of synthetic unnatural α‐amino acid‐based organocatalysts, such as β‐alkyl alanines, alanine‐based phosphines, and tert ‐leucine derivatives, are reviewed herein. The organocatalytic properties of unnatural monocyclic, bicyclic, and tricyclic proline derivatives are also reviewed. Several families of these organocatalysts permit the efficient and stereoselective synthesis of complex natural products. Most of the reviewed organocatalysts accelerate the reported reactions through covalent interactions that raise the HOMO (enamine intermediates) or lower the LUMO (iminium intermediates).