Cyclosulfamide as a chiral auxiliary: application to efficient asymmetric synthesis (alkylation/aldolization)

Fabien Fécourt (1) , Gérald Lopez (1) , Arie van Der Lee (2) , Jean Martinez (1) , Georges Dewynter (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
2 IEM - Institut Européen des membranes

The chiral cyclosulfamide (S)-2-benzyl-4-isopropyl-1,2,5-thiadiazolidine 1,1-dioxide was designed as a chimera of Evans and Oppolzer chiral auxiliaries. The N-propionyl derivative appeared to be very powerful for the stereocontrolled synthesis of chiral building blocks through asymmetric aldolization and alkylation reactions.

Domaines: Cristallographie; Chimie organique

Fabien Fécourt, Gérald Lopez, Arie van Der Lee, Jean Martinez, Georges Dewynter. Cyclosulfamide as a chiral auxiliary: application to efficient asymmetric synthesis (alkylation/aldolization). Tetrahedron: Asymmetry, 2010, 21, pp.2361-2366. ⟨10.1016/j.tetasy.2010.09.001⟩. ⟨hal-00533621⟩