Synthesis of dichloromethyl-substituted salicylates and pyran-4-ones by cyclocondensation of 1,3-bis(silyloxy)-1,3-butadienes with 1,1-dimethoxy-4,4-dichlorobut-1-en-3-one: control of the C,C- and C,O-regioselectivity by the choice of Lewis acid

摘要

The TiCl4-mediated formal [3+3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3 -butadienes with 1,1-dimethoxy-4,4-dichlorobut-1-en-3-one afforded a variety of functionalized 6-dichlorornethyl-4-methoxysalicylates with very good regioselectivity. Some of the products were transformed into 6-formyl-4-methoxysalicylates. The employment of Me3SiOTf instead of TiCl4 resulted in a change of the regioselectivity and in the formation of functionalized 2-(dichloromethyl)pyran-4-ones.