1410775-93-7Relevant articles and documents
Synthesis and Fluorescent Properties of β-Pyridyl α-Amino Acids
Harkiss, Alexander H.,Bell, Jonathan D.,Knuhtsen, Astrid,Jamieson, Andrew G.,Sutherland, Andrew
, p. 2879 - 2890 (2019/03/07)
The preparation of a new class of β-pyridyl α-amino acid is described using a highly regioselective, ytterbium-catalyzed hetero-Diels-Alder reaction of enones with vinyl ethers followed by a modified Knoevenagel-Stobbe reaction as the key heterocycle form
Switching the stereochemical outcome of 6- endo - Trig cyclizations; Synthesis of 2,6- cis -6-substituted 4-oxopipecolic acids
Daly, Mark,Cant, Alastair A.,Fowler, Lindsay S.,Simpson, Graham L.,Senn, Hans Martin,Sutherland, Andrew
, p. 10001 - 10009 (2013/01/15)
A base-mediated 6-endo-trig cyclization of readily accessible enone-derived α-amino acids has been developed for the direct synthesis of novel 2,6-cis-6-substituted-4-oxo-l-pipecolic acids. A range of aliphatic and aryl side chains were tolerated by this mild procedure to give the target compounds in good overall yields. Molecular modeling of the 6-endo-trig cyclization allowed some insight as to how these compounds were formed, with the enolate intermediate generated via an equilibrium process, followed by irreversible tautomerization/neutralization providing the driving force for product formation. Stereoselective reduction and deprotection of the resulting 2,6-cis-6-substituted 4-oxo-l-pipecolic acids to the corresponding 4-hydroxy-l-pipecolic acids was also performed.
