Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines

被引：7

作者：

Garcia-Minguens, Eduardo ^{[1
,2
]}

Ferrandiz-Saperas, Marcos ^{[1
,2
]}

Retamosa, M. de Gracia ^{[1
,2
]}

Najera, Carmen ^{[2
]}

Yus, Miguel ^{[2
]}

Sansano, Jose M. ^{[1
,2
]}

机构：

[1] Univ Alicante, Ctr Innovac Quim Avanzada ORFEO CINQA, Inst Sintesis Organ ISO, Dept Quim Organ, POB 99, San Vicente Del Raspeig 03690, Spain

[2] Ctr Innovac Quim Avanzada ORFEO CINQA, POB 99, San Vicente Del Raspeig 03690, Spain

来源：

MOLECULES | 2022年 / 27卷 / 14期

关键词：

nitroprolinates; enantioseletive cycloaddition; phosphoramidite; azomethine ylides; diamines; AZOMETHINE YLIDES; INHIBITORS; CATALYSTS; PYRROLIDINES; DESIGN;

D O I：

10.3390/molecules27144579

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The enantioselective 1,3-dipolar cycloaddition between imino esters and (Z)-nitroalkenes bearing a masked amino group in the beta-position was studied using several chiral ligands and silver salts. The optimized reaction conditions were directly applied to the study of the scope of the reaction. The determination of the absolute configuration was evaluated using NMR experiments and electronic circular dichroism (ECD). The reduction and hydrolysis of both groups was performed to generate in an excellent enantiomeric ratio the corresponding cis-2,3-diaminoprolinate.

引用

页数：15

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