1,3-OXAZOLIDIN-5-ONES DERIVED FROM PROLINE AS CHIRAL COMPONENTS IN THE SYNTHESIS OF PREDICTIVE ENANTIOSELECTIVE COUPLING REAGENTS

被引：1

作者：

Kasperowicz-Frankowska, Katarzyna ^{[1
]}

Kolesinska, Beata ^{[1
]}

Gzik, Anna ^{[1
]}

Jastrzabek, Konrad ^{[1
]}

Kaminski, Zbigniew J. ^{[1
]}

机构：

[1] Lodz Univ Technol, Inst Organ Chem, Zeromskiego 116, PL-90924 Lodz, Poland

来源：

ACTA POLONIAE PHARMACEUTICA | 2018年 / 75卷 / 04期

关键词：

enantioselective condensation; triazine coupling reagent; peptide synthesis; diirality transfer to nitrogen; chiral nitrogen atom; AMINO-ACIDS; PEPTIDES; ESTER;

D O I：

10.32383/appdr/78726

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

1,3-Oxazolid in-5-ones derived from both enantiomers of proline and trichloroacetaldehyde were prepared and applied as an amine component in the synthesis of chiral predictive triazine-based coupling reagents. The reagents were found to be useful in condensations yielding enantiomerically enriched products from racemic substrates.

引用

页码：921 / 927

页数：7

共 4 条

[1] Synthesis of new chiral N-arylsulfonyl-1,3-oxazolidin-2-ones from α-amino acids
Aliyenne, Ahmed Ould
Kraiem, Jamil
Kacem, Yakdhane
Ben Hassine, Bechir
COMPTES RENDUS CHIMIE, 2007, 10 (03) : 251 - 258
[2] The design, synthesis, and application of a chiral coupling reagent derived from strychnine for the enantioselective activation of a carboxylic group
Kolesinska, Beata
Kasperowicz, Katarzyna
Sochacki, Marek
Mazur, Adam
Jankowski, Stefan
Kaminski, Zbigniew J.
TETRAHEDRON LETTERS, 2010, 51 (01) : 20 - 22
[3] SYNTHESIS OF CHIRAL TRIAZINE COUPLING REAGENTS BASED ON ESTERS OF N-ALKYLPROLINE AND THEIR APPLICATION IN THE ENANTIOSELECTIVE INCORPORATION OF D OR L AMINO ACID RESIDUE DIRECTLY FROM RACEMIC SUBSTRATE
Kasperowicz-Frankowska, Katarzyna
Gzik, Anna
Dziemidkiewicz, Michal
Kolesinska, Beata
Kaminski, Zbigniew J.
ACTA POLONIAE PHARMACEUTICA, 2014, 71 (06): : 994 - 1003
[4] Enantioselective Synthesis of 3,4-Dihydro-1,2-oxazepin-5(2H)-ones and 2,3-Dihydropyridin-4(1H)-ones from β-Substituted β-Hydroxyaminoaldehydes
Ranade, Adwait R.
Georg, Gunda I.
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03) : 984 - 992

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