Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes

被引：5

作者：

Chabour, Ihssene ^{[1
,2
,3
]}

Castello, Luis M. ^{[1
,2
,3
]}

Mancebo-Aracil, Juan ^{[1
,2
,3
]}

Martin-Rodriguez, Maria ^{[1
,2
,3
]}

de Gracia Retamosa, Maria ^{[2
,4
]}

Najera, Carmen ^{[1
,2
]}

Sansano, Jose M. ^{[1
,2
,3
]}

机构：

[1] Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain

[2] Ctr Innovac Quim Avanzada ORFEO CINQA, Madrid, Spain

[3] Univ Alicante, ISO, Apdo 99, E-03080 Alicante, Spain

[4] CSIC US, Inst Invest Quim, Avda Americo Vespucio 49, Seville 41092, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2017年 / 28卷 / 10期

关键词：

DEPENDENT RNA-POLYMERASE; COMPLEXES; MOLECULE;

D O I：

10.1016/j.tetasy.2017.08.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric 1,3-dipolar cycloaddition of an imino ester 5 with tert-butyl acrylate is catalyzed by a dual chiral silver(I) complex formed from a chiral phosphoramidite 14 and the chiral silver(I) binolphosphate (R)-17. This reaction is selected to achieve the synthesis of enantiomerically enriched key structures to access the third generation of GSK HCV inhibitors. The scope of this dual chiral catalytic system is analyzed by employing different imino esters and dipolarophiles, and also compared with the same cycloaddition reactions performed with the chiral phosphoramidite 14 center dot AgClO4 complex. (C) 2017 Elsevier Ltd. All rights reserved.

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页码：1423 / 1429

页数：7

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