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Exploring Chemical Reactivity with Organocatalysis

Objective

The proposed research seeks to redefine the synthetic potential of a fundamental organic transformation: the functionalisation of carbonyl compounds. Today, synthetic chemists can address even the most daunting of challenges connected with the asymmetric catalytic functionalisation of carbonyl compounds at their alpha and beta positions. In contrast, there are no known general strategies for the corresponding direct, catalytic and enantioselective transformation to a carbonyl group at the gamma position.
By developing innovative methodologies to effectively address this issue, I will provide a novel reactivity framework for exploring unprecedented transformations. This would strengthen the chemistry toolbox to better face the challenges of modern organic chemistry.
I will proceed by combining asymmetric aminocatalysis (a versatile chemical strategy whose potential has not yet been fully explored) with photoredox catalysis driven by visible light. This will provide access to open-shell radical species, which participate in bond constructions that are unavailable using amine organocatalysis alone. Since electron-deficient radicals are known to rapidly react with pi-rich olefins to forge even the most elusive C-C bonds, mild and catalytic approaches to accessing these reaction manifolds offer desirable opportunities for designing new gamma-functionalisations of carbonyl compounds. Developing an innovative system based on a chiral organic catalyst that efficiently harnesses the energy of solar radiation is in line with the European approach to attaining Sustainable Chemistry, one of the central scientific goals of the 21st Century.
This proposal challenges the current paradigms for stereoselective functionalisation by providing a template for directly functionalising unmodified carbonyl compounds at their gamma positions, expanding the way chemists think about making chiral molecules

Field of science

  • /natural sciences/chemical sciences/organic chemistry
  • /natural sciences/earth and related environmental sciences/atmospheric sciences/meteorology/solar radiation

Call for proposal

ERC-2011-StG_20101014
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Funding Scheme

ERC-SG - ERC Starting Grant

Host institution

FUNDACIO PRIVADA INSTITUT CATALA D'INVESTIGACIO QUIMICA
Address
Avenida Paissos Catalans 16
43007 Tarragona
Spain
Activity type
Research Organisations
EU contribution
€ 1 500 000
Principal investigator
Paolo Melchiorre (Prof.)
Administrative Contact
Eva María Alcazar Exposito (Dr.)

Beneficiaries (1)

FUNDACIO PRIVADA INSTITUT CATALA D'INVESTIGACIO QUIMICA
Spain
EU contribution
€ 1 500 000
Address
Avenida Paissos Catalans 16
43007 Tarragona
Activity type
Research Organisations
Principal investigator
Paolo Melchiorre (Prof.)
Administrative Contact
Eva María Alcazar Exposito (Dr.)