Formal Asymmetric (4+1) Annulation Reaction between Sulfur Ylides and 1,3-Dienes

Rousseau, Olivier; Delaunay, Thierry; Dequirez, Geoffroy; Tran, Trieu-Van; Robeyns, Koen; Robiette, Raphaël

doi:10.1002/chem.201502579

Formal Asymmetric (4+1) Annulation Reaction between Sulfur Ylides and 1,3-Dienes

Rousseau, Olivier

;

Delaunay, Thierry

;

Dequirez, Geoffroy

;

Tran, Trieu-Van

;

Robiette, Raphaël

;et.al.

(2015) Chemistry: A European Journal — Vol. 21, n° 37, p. 12899-12902 (2015)

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Authors

Rousseau, OlivierUCLouvain
Author
Delaunay, ThierryUCLouvain
Author
Dequirez, GeoffroyUCLouvain
Author
Tran, Trieu-VanUCLouvain
Author
Robeyns, KoenUCLouvain
Author
Robiette, RaphaëlUCLouvain
Author

Abstract

A highly enantioselective synthesis of functionalized cyclopentanoids by a formal asymmetric (4+1) annulation strategy was developed. The methodology consists in a stereoselective cyclopropanation reaction between chiral sulfur ylides and 1,3-dienes followed by a, in situ, stereospecific MgI2-catalyzed rearrangement of vinylcyclopropanes. This method is distinguished by a remarkable compatibility with functional groups and a high stereocontrol.

Affiliations

UCLouvainSST/IMCN/MOST - Molecular Chemistry, Materials and Catalysis

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Rousseau, O., Delaunay, T., Dequirez, G., Tran, T.-V., Robeyns, K., & Robiette, R. (2015). Formal Asymmetric (4+1) Annulation Reaction between Sulfur Ylides and 1,3-Dienes. Chemistry: A European Journal, 21(37), 12899-12902. https://doi.org/10.1002/chem.201502579 (Original work published 2015)