130264-65-2Relevant academic research and scientific papers
Stereoselective Free-Radical Cyclization on a Sugar Template The Suphonyl Radical as a Synthetic Tool for Functionalized Glycosides
Nouguier, Robert,Lesueur, Catherine,Riggi, Enzo de,Bertrand, Michele Paula,Virgili, Albert
, p. 3541 - 3544 (1990)
The addition of a sulphonyl radical to the external double bond of an allyl glycal generates a pro-chiral carbon radical which adds to the glycal double bond with a high diastereoselectivity.Through three consecutive radical steps, the configurations of three new asymmetric centers are controlled.
Stereocontrol in radical cyclizations on sugar templates
Lesueur, Catherine,Nouguier, Robert,Bertrand, Michele Paula,Hoffmann, Pascale,De Mesmaeker, Alain
, p. 5369 - 5380 (2007/10/02)
The radical cyclization of alkyl hex-2-enopyranosides provides a stereocontrolled route to fused furanopyranes. The intermediate radical is generated either via the reduction of the appropriate halide by tin hydride or via sulfonyl radical addition to allyl hex-2-enopyranosides. The two methodologies are compared with respect to diastereoselectivity. Stereocontrol is discussed on the basis of conformational preference in the transition state.
