99277-38-0Relevant academic research and scientific papers
Synthetic Studies on Spiroketal Natural Products. II. An Enantioselective Synthesis of (R)- and (S)-1,7-Dioxaspiroundecane
Iwata, Chuzo,Fujita, Masahiro,Kuroki, Toshio,Hattori, Kohji,Uchida, Shuji,Imanishi,Takeshi
, p. 3257 - 3263 (2007/10/02)
Both enantiomers of 1,7-dioxaspiroundecane, a chiral compound with C2 symmetry, were stereoselectively synthesized from an (R)-sulfoxide compound 8.The reaction of menthyl (S)-p-toluenesulfinate with a Grignard reagent gave the chiral sulfoxide (8), which was derived to a dihydropyran (12) by a several-step sequence.The base-catalyzed intramolecular Michael reaction of 12 exclusively afforded a dioxaspiro product (13) as a single stereoisomer.An acidic treatment of 13 resulted in isomerisation of the spiro center to give 14.Desulfurization of 13 and 14 over Raney nickel in the presence of sodium hydroxide gave (R)- and (S)-1,7-dioxaspiroundecane (R-1 and S-1), respectively. Keywords---asymmetric synthesis; chiral sulfoxide; insect pheromone; C2-symmetry; spiroketal; intramolecular Michael addition; 1,7-dioxaspiroundecane
INTRAMOLECULAR MICHAEL ADDITION REACTION TO CHIRAL VINYLIC SULFOXIDES. AN ENANTIOSELECTIVE SYNTHESIS OF (R)- AND (S)-1,7-DIOXASPIROUNDECANE
Iwata, Chuzo,Fujita, Masahiro,Hattori, Kohji,Uchida, Shuji
, p. 2221 - 2224 (2007/10/02)
(R)- and (S)-1,7-Dioxaspiroundecane , sex pheromone of an olive fly, was each stereoselectively synthesized using an intramolecular Michael addition of hydroxyl group to a chiral vinylic sulfoxide moiety as an asymmetric induction step.
