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2005
Rings with 7 or more members
Q 0050
Efficient Access to Functionalized Medium-Ring Systems by Radical Fragmentation/Radical Addition to α-Iodoketones. — The transformation of bicyclic tertiary
37- 064 hydroxyketals
into medium ring containing α-iodo diketones is achieved via CAN-catalyzed deprotection of bicyclic hydroxyacetals followed by oxidative radical fragmentation in the presence of iodine. Deiodination of product (III) can be achieved by tin
hydride in the presence of AIBN. When ester (V) is added to the reaction mixture this
process can be extended to the preparation of α,β-unsaturated esters such as (VI) and
(XVI). — (DE DOBBELEER, C.; ATES, A.; VANHERK, J.-C.; MARKO*, I. E.;
Tetrahedron Lett. 46 (2005) 22, 3889-3893; Dep. Chim., Univ. Cathol. Louvain,
B-1348 Louvain-la-Neuve, Belg.; Eng.) — Mais
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