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

Giulia Rainoldi; Fabio Begnini; Mariska De Munnik; Leonardo Lo Presti; Christophe M.L. Vande Velde; Romano Orru; Giordano Lesma; Eelco Ruijter; Alessandra Silvani

doi:10.1021/acscombsci.7b00179

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

Giulia Rainoldi^*
, Fabio Begnini
, Mariska De Munnik
, Leonardo Lo Presti
, Christophe M.L. Vande Velde
, Romano Orru
, Giordano Lesma
, Eelco Ruijter
, Alessandra Silvani

^*Corresponding author for this work

AIMMS

Research output: Contribution to Journal › Article › Academic › peer-review

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Abstract

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-Joullié and the azido-Ugi reactions resulted highly diastereoselective, affording predominantly the trans-configured products, as confirmed by X-ray crystallographic analysis.

Original language	English
Pages (from-to)	98-105
Number of pages	8
Journal	ACS Combinatorial Science
Volume	20
Issue number	2
DOIs	https://doi.org/10.1021/acscombsci.7b00179
Publication status	Published - 12 Feb 2018

Funding

We thank Elwin Janssen for technical assistance, Jürrien Collet and John Braun for HRMS measurements, Kristof Van Hecke (UGent) for X-ray data collection of 5{1,1}, and the Hercules Foundation (project AUGE/11/029 “3D-SPACE: 3D Structural Platform Aiming for Chemical Excellence”) for funding of the diffractometer.

Funders	Funder number
Hercules Foundation	AUGE/11/029

Keywords

Asinger reaction
azido-Ugi reaction
multicomponent reactions
spirooxindole
thiazolidine
Ugi-Joullié reaction

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10.1021/acscombsci.7b00179

Sequential Multicomponent Strategy for the Diastereoselective Synthesis of Densely Functionalized Spirooxindole-Fused ThiazolidinesFinal published version, 3.32 MBLicence: Article 25fa Dutch Copyright Act

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@article{044abadd7ca8485095b7466d91819aed,

title = "Sequential Multicomponent Strategy for the Diastereoselective Synthesis of Densely Functionalized Spirooxindole-Fused Thiazolidines",

abstract = "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-Joulli{\'e} and the azido-Ugi reactions resulted highly diastereoselective, affording predominantly the trans-configured products, as confirmed by X-ray crystallographic analysis.",

keywords = "Asinger reaction, azido-Ugi reaction, multicomponent reactions, spirooxindole, thiazolidine, Ugi-Joulli{\'e} reaction",

author = "Giulia Rainoldi and Fabio Begnini and \{De Munnik\}, Mariska and \{Lo Presti\}, Leonardo and \{Vande Velde\}, \{Christophe M.L.\} and Romano Orru and Giordano Lesma and Eelco Ruijter and Alessandra Silvani",

year = "2018",

month = feb,

day = "12",

doi = "10.1021/acscombsci.7b00179",

language = "English",

volume = "20",

pages = "98--105",

journal = "ACS Combinatorial Science",

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publisher = "American Chemical Society",

number = "2",

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TY - JOUR

T1 - Sequential Multicomponent Strategy for the Diastereoselective Synthesis of Densely Functionalized Spirooxindole-Fused Thiazolidines

AU - Rainoldi, Giulia

AU - Begnini, Fabio

AU - De Munnik, Mariska

AU - Lo Presti, Leonardo

AU - Vande Velde, Christophe M.L.

AU - Orru, Romano

AU - Lesma, Giordano

AU - Ruijter, Eelco

AU - Silvani, Alessandra

PY - 2018/2/12

Y1 - 2018/2/12

N2 - 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-Joullié and the azido-Ugi reactions resulted highly diastereoselective, affording predominantly the trans-configured products, as confirmed by X-ray crystallographic analysis.

AB - 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-Joullié and the azido-Ugi reactions resulted highly diastereoselective, affording predominantly the trans-configured products, as confirmed by X-ray crystallographic analysis.

KW - Asinger reaction

KW - azido-Ugi reaction

KW - multicomponent reactions

KW - spirooxindole

KW - thiazolidine

KW - Ugi-Joullié reaction

UR - https://www.scopus.com/pages/publications/85041902438

UR - https://www.scopus.com/pages/publications/85041902438#tab=citedBy

U2 - 10.1021/acscombsci.7b00179

DO - 10.1021/acscombsci.7b00179

M3 - Article

AN - SCOPUS:85041902438

SN - 2156-8952

VL - 20

SP - 98

EP - 105

JO - ACS Combinatorial Science

JF - ACS Combinatorial Science

IS - 2

ER -

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

Abstract

Funding

Keywords

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CCDC 1555670: Experimental Crystal Structure Determination

CCDC 1555553: Experimental Crystal Structure Determination

Cite this

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

Abstract

Funding

Keywords

Access to Document

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Other files and links

Fingerprint

Datasets

CCDC 1555670: Experimental Crystal Structure Determination

CCDC 1555553: Experimental Crystal Structure Determination

Cite this