Enolate addition to a 2-alkylidene[1,3]dithiane-derived bissulfoxide. A new a(2)-acceptor.
Reaction of enolates derived from esters and ketones to an easily prepared alkylidene[1,3]dithiane-1,3-dioxide afforded the respective adducts with good yields and selectivities generally exceeding 85:15. The base used for enolate addition played no significant role for the reaction outcome, and addition of a silyl enole ether gave similar results. The thus formed oxygenated S,S-acetals were transformed into the corresponding 1,4-dicarbonyls by a reduction/oxidation sequence with 84% yield. [reaction: see text]
Wedel
Tobias
T
Institut für Organische Chemie, Universität Karlsruhe (TH), Karlsruhe 76131, Germany.
Podlech
Joachim
J