Stereoselective Synthesis of Medium-Sized Cyclic Compounds by Means of Tandem Reactions of a Cyclic Oxosulfonium Ylide with Acetates of Baylis−Hillman Adducts

Recent Advances in the Baylis−Hillman Reaction and Applications

“…Fujimoto and co-workers , reported a tandem Michael-intramolecular Corey−Chaykovsky reaction of the five-membered cyclic oxosulfonium ylide with acetates of the Baylis−Hillman adducts in the presence of base-producing cycloheptene oxide derivatives 260 as a single stereoisomer. However, in the case of six-membered oxosulfonium ylide, the cyclooctane oxide derivatives 261 were obtained as a mixture of stereoisomers in moderate yields (Scheme ).…”

Recent Advances in the Baylis−Hillman Reaction and Applications

“…Fujimoto and co-workers , reported a tandem Michael-intramolecular Corey−Chaykovsky reaction of the five-membered cyclic oxosulfonium ylide with acetates of the Baylis−Hillman adducts in the presence of base-producing cycloheptene oxide derivatives 260 as a single stereoisomer. However, in the case of six-membered oxosulfonium ylide, the cyclooctane oxide derivatives 261 were obtained as a mixture of stereoisomers in moderate yields (Scheme ).…”

Recent Developments in the Chemistry of Polyvalent Iodine Compounds

“…Arylations with aryliodonium salts can be effectively catalyzed by transition metals. − The arylation of the lithium enolates of cyclic ketones with diphenyliodonium triflate in the presence of stoichiometric quantities of copper cyanide afford the corresponding α-phenylated ketones in moderate yields . Likewise, the copper-catalyzed arylation of tetrahydrothiophene selectively affords cyclic S -phenyl sulfonium salt, a key precursor to the important oxosulfonium ylides …”

Recent Advances in the Baylis−Hillman Reaction and Applications

“…Fujimoto and co-workers , reported a tandem Michael-intramolecular Corey−Chaykovsky reaction of the five-membered cyclic oxosulfonium ylide with acetates of the Baylis−Hillman adducts in the presence of base-producing cycloheptene oxide derivatives 260 as a single stereoisomer. However, in the case of six-membered oxosulfonium ylide, the cyclooctane oxide derivatives 261 were obtained as a mixture of stereoisomers in moderate yields (Scheme ).…”

Recent Developments in the Chemistry of Polyvalent Iodine Compounds

“…Arylations with aryliodonium salts can be effectively catalyzed by transition metals. − The arylation of the lithium enolates of cyclic ketones with diphenyliodonium triflate in the presence of stoichiometric quantities of copper cyanide afford the corresponding α-phenylated ketones in moderate yields . Likewise, the copper-catalyzed arylation of tetrahydrothiophene selectively affords cyclic S -phenyl sulfonium salt, a key precursor to the important oxosulfonium ylides …”

Recent Advances in the Baylis−Hillman Reaction and Applications

“…Fujimoto and co-workers , reported a tandem Michael-intramolecular Corey−Chaykovsky reaction of the five-membered cyclic oxosulfonium ylide with acetates of the Baylis−Hillman adducts in the presence of base-producing cycloheptene oxide derivatives 260 as a single stereoisomer. However, in the case of six-membered oxosulfonium ylide, the cyclooctane oxide derivatives 261 were obtained as a mixture of stereoisomers in moderate yields (Scheme ).…”

Recent Developments in the Chemistry of Polyvalent Iodine Compounds

“…Arylations with aryliodonium salts can be effectively catalyzed by transition metals. − The arylation of the lithium enolates of cyclic ketones with diphenyliodonium triflate in the presence of stoichiometric quantities of copper cyanide afford the corresponding α-phenylated ketones in moderate yields . Likewise, the copper-catalyzed arylation of tetrahydrothiophene selectively affords cyclic S -phenyl sulfonium salt, a key precursor to the important oxosulfonium ylides …”