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Enantioselective carbocyclizations towars the synthesis of compounds with biological activity

Title: "Enantioselective carbocyclizations towards the synthesis of compounds with biological activity"

Reference: CTQ2016-76782-P

Main researcher 1: Carmen Nájera Domingo                

Main researcher 2: José Miguel Sansano Gil               

Type: R & D Project

Start date: 30/12/2016

End date: 29/12/2019

Total granted: 145.200,00 €

ERDF total available: 145.200,00 €

Sponsor Agency: Spanish Ministry of Economy, Industry and Competitiveness with ERDF funds and funds from the State Research Agency (AEI).

The presented proposal deals with the development of new carbocyclization procedures catalyzed by chiral transition metal complexes bearing privileged ligands and by chiral Brønsted acids. The main objectives are:

1. The development of new imino esters, derived form alpha-aminoboronic acids, to test the enantioselective 1,3-DC, which allow the preparation of new proline homologous borylated at the 2-position.

2. To study the multicomponent enantioselective 1,3-DC using iminium cations, derived from amino esters bearing an acyclic or cyclic secondary amine.

3. The employment of allyl and benzyl imines in C-H activation to give azomethine ylides.

4. To survey the intermolecular multicomponent [4+2] cycloaddition of the amine-aldehyde-dienophile (AAD) which the corresponding enantioselective version has not been described.

5. To test  the intermolecular asymmetric allylic alkylation (AAA) under palladium catalysis of 3-acetylindoles to essay asymmetric deacylative allylation (DcA) of 3-acetyloxindoles.

6. To develop the intramolecular AAA with different 2- and 3-substituted indoles bearing an allylic alcohol unit would allow the synthesis of fused polycyclic indoles .


Department of Organic Chemistry

Universidad de Alicante
Facultad de Ciencias, Fase I
Carretera de San Vicente del Raspeig S/N
03690 San Vicente del Raspeig
Alicante (Spain)

Tel: (+34) 96 590 3549

Fax: (+34) 96 590 3549

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Carretera San Vicente del Raspeig s/n - 03690 San Vicente del Raspeig - Alicante - Tel. 96 590 3400 - Fax 96 590 3464