Consecutive reactions with sulfoximines: a direct access to 2-sulfonimidoylylidene tetrahydrofurans and 6-sulfonimidoylmethyl- 3,4-dihydro-2H-pyrans

Marie-Alice Virolleaud (1) , Vellaisamy Sridharan (1) , Damien Mailhol (1) , Damien Bonne (1) , Cyril Bressy (1) , Gaëlle Chouraqui (1) , Laurent Commeiras (1) , Yoann Coquerel (1) , Jean Rodriguez (1)

1 STeRéO

2-Sulfonimidoylylidene tetrahydrofurans and 2-sulfonimidoylylidene-5-vinyl tetrahydrofurans were readily synthesized via a consecutive acylation/SN2 sequence with total regio- and chemoselectivity from Johnson's sulfoximine derivatives. The same consecutive reaction could also be applied to the expeditious synthesis of 6-sulfonimidoylmethyl-3,4-dihydro-2H-pyrans.

Mots clés: domino reaction; sulfoximine; chiral sulfur; dianion; oxygen-heterocycles

Domaines: Chimie organique

Marie-Alice Virolleaud, Vellaisamy Sridharan, Damien Mailhol, Damien Bonne, Cyril Bressy, et al.. Consecutive reactions with sulfoximines: a direct access to 2-sulfonimidoylylidene tetrahydrofurans and 6-sulfonimidoylmethyl- 3,4-dihydro-2H-pyrans. Tetrahedron, 2009, 65, pp.9756-9764. ⟨10.1016/j.tet.2009.09.080⟩. ⟨hal-00676864⟩