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The 1,5-HAT-1,2-(ester)alkyl radical migration (Surzur-Tanner rearrangement) radical/polar sequence triggered by alkoxyl radicals has been studied on a series of C -glycosyl substrates with 3- C -(α,β-d,l-glycopyranosyl)1-propanol and C -(α-d,l-glycopyranosyl)methanol structures prepared from chiral pool d- and l-sugar. The use of acetoxy and diphenoxyphosphatoxy as leaving groups provides an efficient construction of 10-deoxy-1,6-dioxaspiro[4.5]decane and 4-deoxy-6,8-dioxabicyclo[3.2.1]octane frameworks. The alkoxyl radicals were generated by the reaction of the corresponding N -alkoxyphthalimides with group 14 hydrides [ n -Bu 3 SnH(D) and (TMS) 3 SiH], and in comparative terms, the reaction was also initiated by visible light photocatalysis using the Hantzsch ester/ fac -Ir(ppy) 3 procedure. Special attention was devoted to the influence of the relative stereochemistry of the centers involved in the radical sequence on the reaction outcome. The addition of BF 3 •Et 2 O as a catalyst to the radical sequence resulted in a significant increase in the yields of the desired bicyclic ketals.

journal of organic chemistry

1,5-Hydrogen Atom Transfer/Surzur–Tanner Rearrangement: A Radical Cascade Approach for the Synthesis of 1,6-Dioxaspiro[4.5]decane and 6,8-Dioxabicyclo[3.2.1]octane Scaffolds in Carbohydrate Systems