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Unprecedented strategies for accessing functionalized four-membered heterocycles

A part of our research focuses on unprecedented strategies to access enantioenriched alkylidenecyclobutanes (ACBs) and cyclobutenes (CBs).

Stereospecific boron-homologations and stereoselective allylborations have been successfully combined into a single-pot sequence to generate targeted molecules with up to 99% ee.

Angew. Chem. Int. Ed. 2015

Org. Lett. 2016

Chem. Eur. J. 2017

Org. Lett. 2017

Synthesis 2018

Azetidines, oxetanes and thietanes have demonstrated their potential as core motifs in medicinal chemistry.

Our objective was to make these motifs easily accessible.

Through new and innovative strategies, we aim to elaborate unique methodologies that will allow for a high degree of functionalization.

Org. Lett. 2017

Org. Lett. 2018

Expedient routes towards strained fused ring systems

In the course of our study on efficient strategies towards sophisticated alkylidenecyclobutanes, we found that fused ACBs - direct analogues of protoilludanes - were

to possess anti-leukemia properties. A very simple but efficient route was designed to access these functionalized structures in high diastereomeric purities and requiring a single purification step.

Org. Lett. 2017

Org. Lett. 2018

J. Org. Chem. 2018

Boron-relayed C-C bond forming reactions

This part of our research program focuses on C-C bond formation using organoboron derivatives.

Investigations conducted on Zweifel olefination are at the origin of the following research axes.

In situ formation of bisorganoborinates

Simple and practical sequences for the in situ formation of bisorganiborinates has been developed to provide alternatives to the use of expensive and poorly available reagents.

These sequences involve both coordination and ligand exchange step at the boron center.

Org. Lett. 2019

Novel organocerium species

Organolithium species show great efficiency in Zweifel olefinations. More functional group tolerant species such as organomagnesium are less efficient in this transformation.

With an electronegativity value between lithium and magnesium, the abondant cerium atom was employed as a dependable alternative in the formation of organocerium species through unprecedented triple halogen-cerium exchanges.

Angew. Chem. Int. Ed. 2019

Synlett 2019 (review)

Extending the scope beyond Zweifel olefination

Inspired by Zweifel olefination, a new reaction path was envisioned.

Organoborate salts were designed to allow for a catalyst-free electrocoupling reaction.

The scope includes - so far - aryl-aryl, aryl-heteroaryl and olefin coupling reactions.

J. Am. Chem. Soc. 2020

Chem. Eur. J. 2020