731810-63-2Relevant academic research and scientific papers
Access to enantiomerically pure cis- and trans-β-phenylproline by high-performance liquid chromatography resolution
Fatás, Paola,Gil, Ana M.,Calaza, M. Isabel,Jiménez, Ana I.,Cativiela, Carlos
, p. 1082 - 1091 (2013/02/22)
The preparation of all four stereoisomers of the proline analog that bears a phenyl group attached to the β carbon either cis or trans to the carboxylic acid (cis- and trans-β-phenylproline, respectively) has been addressed. The methodology developed allows access to multigram quantities of the target amino acids in enantiomerically pure form and suitably protected for use in peptide synthesis. Racemic precursors of cis-β-phenylproline and trans-β-phenylproline were prepared from easily available starting materials and subjected to high-performance liquid chromatography enantioseparation. Semipreparative columns (250 × 20 mm) containing chiral stationary phases based on amylose (Chiralpak IA) (Daicel-Chiral Technologies Europe, Illkirch, France) or cellulose (Chiralpak IC) were used respectively for the resolution of the cis- and trans-β-phenylproline precursors. Chirality, 24:1082-1091, 2012. 2012 Wiley Periodicals, Inc. Copyright
Asymmetric synthesis of proline-based conformationally constrained tryptophan mimetic
Delaye, Pierre-Olivier,Vasse, Jean-Luc,Szymoniak, Jan
supporting information; experimental part, p. 3635 - 3637 (2010/09/06)
The synthesis of an optically pure proline-based tryptophan mimetic is described. The strategy involves the in situ generation of an unprecedented allylmetal species containing the indole moiety, and its coupling with a chiral imine. The construction of the 3-substitued proline skeleton is then achieved through a hydrozirconation/iodination sequence applied to the resulting homoallylic amine.
