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2005
Oxidation
O 0212
25- 042
Remarkable Selectivity in Addition of Alcohols to Epoxydienes of 5,7-Bicyclic and
5,7,6-Tricyclic Systems. — Tricyclic epoxydienes like (II) are found to undergo regioand stereoselective 1,6-addition with alcohols. Starting from bicyclic epoxyalkenes
generated from dienes (VIII), 1,4-addition products are formed regio- and stereoselectively. The reaction of the homologues (XI) proceeds without diastereoselectivity and
sometimes 1,2-addition also takes place. The simple vinyloxiranes (XIV) and (XVII)
give predominantly or exclusively 1,2-addition products. These results indicate that the
structure strongly affects the reaction outcome. — (BOYER, F.-D.; HANNA*, I.;
J. Org. Chem. 70 (2005) 3, 1077-1080; Lab. Synth. Org., CNRS, DCSO, Ec.
Polytech., F-91128 Palaiseau, Fr.; Eng.) — Jannicke
2005
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