Sequential Multicomponent Strategy for the Diastereoselective Synthesis of Densely Functionalized Spirooxindole-Fused Thiazolidines

被引：21

作者：

Rainoldi, Giulia ^{[1
]}

Begnini, Fabio ^{[2
]}

de Munnik, Mariska ^{[3
,4
]}

Lo Presti, Leonardo ^{[1
]}

Vande Velde, Christophe M. L. ^{[5
]}

Orru, Romano ^{[3
,4
]}

Lesma, Giordano ^{[1
]}

Ruijter, Eelco ^{[3
,4
]}

Silvani, Alessandra ^{[1
]}

机构：

[1] Univ Milan, Dipartimento Chim, Via Golgi 19, I-20133 Milan, Italy

[2] Uppsala Univ, Dept Chem BMC, Box 576, SE-75123 Uppsala, Sweden

[3] Vrije Univ Amsterdam, Dept Chem & Pharmaceut Sci, De Boelelaan 1108, NL-1081 HZ Amsterdam, Netherlands

[4] Vrije Univ Amsterdam, AIMMS, De Boelelaan 1108, NL-1081 HZ Amsterdam, Netherlands

[5] Univ Antwerp, Fac Appl Engn, Adv Reactor Technol, Groenenborgerlaan 171, B-2020 Antwerp, Belgium

来源：

ACS COMBINATORIAL SCIENCE | 2018年 / 20卷 / 02期

关键词：

thiazolidine; spirooxindole; multicomponent reactions; Asinger reaction; Ugi-Joullie reaction; azido-Ugi reaction; DIVERSITY-ORIENTED SYNTHESIS; SUBSTITUTED PROLYL PEPTIDES; UGI 3-COMPONENT REACTION; DRUG DISCOVERY; STEREOSELECTIVE-SYNTHESIS; CYCLIC IMINES; DERIVATIVES; ISATIN; TETRAZOLES; SCAFFOLDS;

D O I：

10.1021/acscombsci.7b00179

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We developed two Ugi-type three-component reactions of spirooxindole-fused 3-thiazolines, isocyanides, and either carboxylic acids or trimethylsilyl azide, to give highly functionalized spirooxindole-fused thiazolidines. Two diverse libraries were generated using practical and robust procedures affording the products in typically good yields. The obtained thiazolidines proved to be suitable substrates for further transformations. Notably, both the Ugi-Joullie and the azido-Ugi reactions resulted highly diastereoselective, affording predominantly the trans-configured products, as confirmed by X-ray crystallographic analysis.

引用

页码：98 / 105

页数：8

共 40 条

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