1197335-41-3Relevant academic research and scientific papers
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.
A one-pot, reductive amination/6-endo-trig cyclisation for the stereoselective synthesis of 6-substituted-4-oxopipecolic acids
Fowler, Lindsay S.,Thomas, Lynne H.,Ellis, David,Sutherland, Andrew
supporting information; experimental part, p. 6569 - 6571 (2011/06/26)
The first stereoselective synthesis of 2,6-trans-6-substituted-4-oxo-l- pipecolic acids using a tandem reductive amination/6-endo-trig cyclisation process is described. The sequential reduction and cyclisation mediated by sodium cyanoborohydride allowed the preparation of a series of highly functionalised 6-alkyl and 6-aryl analogues.
Synthesis of fluorescent enone derived α-amino acids
Fowler, Lindsay S.,Ellis, David,Sutherland, Andrew
experimental part, p. 4309 - 4316 (2009/12/06)
The development of a facile and general method for the preparation of enone derived α-amino acids is described. The key step involves a Horner-Wadsworth-Emmons reaction between an aspartic acid derived β-keto phosphonate ester and a range of aldehydes resulting in the formation of highly functionalised α-amino acids in good yields. An efficient two-stage deprotection process using mild conditions was developed to give the parent α-amino acids. Application of this methodology has produced a novel fluorescent α-amino acid that has potential as a biological marker.
