Ribeiro, Adriana Santos’s team published research in Tetrahedron: Asymmetry in 1999-09-24 | CAS: 50966-69-3

Tetrahedron: Asymmetry published new progress about Esterification. 50966-69-3 belongs to class alcohols-buliding-blocks, name is 3-(1H-Pyrrol-1-yl)propan-1-ol, and the molecular formula is C7H11NO, Application of 3-(1H-Pyrrol-1-yl)propan-1-ol.

Ribeiro, Adriana Santos published the artcileSynthesis of (R)-(-) and (S)-(+)-3-(1-pyrrolyl)propyl N-(3,5-dinitrobenzoyl)-α-phenylglycinate and derivatives. A suitable chiral polymeric phase precursor, Application of 3-(1H-Pyrrol-1-yl)propan-1-ol, the main research area is phenylglycine N dinitrobenzoyl derivative enantiomeric preparation; pyrrolylpropyl dinitrobenzoylphenylglycinate preparation precursor polymeric film.

A synthetic route to obtain 3-(1-pyrrolyl)propyl (R)- and (S)-N-(3,5-dinitrobenzoyl)-α-phenylglycinate (1, 2) and derivatives is described. In a first step, pyrrole derivatives were prepared using the Clauson-Kaas method. The esterification, second step, was performed using basic conditions due to sensitivity of the pyrrole group toward acidic conditions. A tautomeric equilibrium involving the stereogenic center induces the product epimerization. The substitution of DMAP and Et3N by a highly hindered base, proton-sponge, furnished the final products without racemization. The enantiomeric excess of 1, 2 and of the corresponding Me esters (3 and 4) were determined by 1H NMR anal. in the presence of optically active Eu(tfc)3. Epimerization was not observed in the preparation of the amine salts of (R)- and (S)-N-(3,5-dinitrobenzoyl)-α-phenylglycine with triethylamine and 1-[3-(dimethylamino)propyl]pyrrole.

Tetrahedron: Asymmetry published new progress about Esterification. 50966-69-3 belongs to class alcohols-buliding-blocks, name is 3-(1H-Pyrrol-1-yl)propan-1-ol, and the molecular formula is C7H11NO, Application of 3-(1H-Pyrrol-1-yl)propan-1-ol.

Referemce:
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