A. Martinezgrau et J. Marcocontelles, CARBOCYCLES FROM CARBOHYDRATES VIA FREE-RADICAL CYCLIZATIONS - NEW SYNTHETIC APPROACHES TO GLYCOMIMETICS, Chemical Society reviews, 27(2), 1998, pp. 155-162
Free radical cyclization of enantiomerically pure, acyclic presursors
derived from carbohydrates is an excellent method for the synthesis of
complex, densely functionalized chiral carbohydrate mimics ('glycomim
etics'). The extent of the acyclic diastereoselection can be modulated
and is closely associated with the structure, rigidity and conformati
onal aspects of the radical precursors, General models for a rationale
of the stereochemical outcome of the cyclizations are shown.