91897-74-4Relevant articles and documents
Synthesis of cis-2,6-tetrahydropyran-4-one via diastereoselectively intramolecular cyclization of β-hydroxy allyl ketone
Lee, Adam Shih-Yuan,Lin, Li-Shin,Chang, Yu-Ting
, p. 3915 - 3919 (2012/07/14)
A series of cis-2,6-tetrahydropyran-4-ones was synthesized from the intramolecular cyclization reaction of β-hydroxy allyl ketones in the presence of Me3SiOTf as catalyst. The β-hydroxy allyl ketone was prepared from allylation reaction with β-hydroxynitrile without protection of hydroxy functionality under the Barbier-type reaction condition.
Carbometalation of cyclopropenes. Stereoselective synthesis of divinyl ketones via 1,5-hydrogen migration reaction of vinylcyclopropanes
Kubota, Katsumi,Isaka, Masahiko,Nakamura, Eiichi
, p. 565 - 574 (2007/10/03)
Stereoselective addition of a vinyl cuprate reagent to a cyclopropenone acetal (2) followed by in situ electrophilic trapping with an alkylating agent affords a cis-1-alkyl-2-vinylcyclopropanone acetal (3), which then undergoes thermal 1,5-hydrogen migrat
PALLADIUM-CATALYZED CROSS-COUPLING OF VINYL IODIDES WITH ORGANOSTANNANES: SYNTHESIS OF UNSYMMETRICAL DIVINYL KETONES.
Goure,Wright,Davis,Labadie,Stille
, p. 6417 - 6422 (2007/10/18)
The palladium-catalyzed cross-coupling reaction of vinyl iodides with trimethyl- or tributylvinylstannanes in the presence of carbon monoxide gives unsymmetrical divinyl ketones in good yields. The reaction conditions are neutral and mild enough (40-50 degree C, 15-50 psig carbon monoxide) that other functional groups in either coupling partner can be brought unaltered into the coupled product. The E geometry in both partners is retained in the coupling product, and the Z geometry in the vinyltin reagent is maintained during the coupling reaction, but the coupled product undergoes slow Z to E isomerization under the usual reaction conditions. Isomerization of the divinyl ketone in the reaction medium is slowed in the dark. The reaction rate is especially sensitive to substituents on the vinyltin reagent, probably as a result of steric hindrance in the transmetalation step of the catalytic cycle.