51905-49-8Relevant academic research and scientific papers
Studies of diastereoselectivity in Diels-Alder reactions of enantiopure (SS)-2-(p-tolylsulfinyl)-l,4-naphthoquinone and chiral racemic acyclic dienes
Carmen Carreno,Garcia-Cerrada, Susana,Urbano, Antonio,Di Vitta, Claudio
, p. 4355 - 4363 (2007/10/03)
Enantiopure sulfinylnaphthoquinone (+)-5 reacted with racemic acyclic dienes 1a-f bearing a stereogenic allylic center, through a tandem cycloaddition/pyrolytic sulfoxide elimination, to afford optically enriched compounds 8a-f and 9a-f with good like/unlike selectivities (ca. 75:25) and good enantiomeric excesses (68-82%), arising from the partial kinetic resolution of the racemic dienes. The opposite diastereoselection (8g-i: 9g- i, up to 5:95)was observed in reactions with dienes 1g-i, having an additional methyl group at C-3, the enantiomeric purities being moderate (14- 25%). Steric effects and torsional interactions in the corresponding approaches account for the observed diastereoselectivities.
ACYLATION OF 1,3-ALKADIENES BY ACYL FLUOROSULFONATES. STEREOSPECIFIC SYNTHESIS OF E AND Z ISOMERS OF CONJUGATED DIENONES
Gavrishova, T.I.,Shastin, A.V.,Balenkova, E.S.
, p. 580 - 583 (2007/10/02)
Acyl fluorosulfonates generated from acyl fluorides and SO3 permits acylation of butadiene and isoprene to give triconjugated dienones.This reaction proceeds stereospecifically and leads to E isomers of the corresponding dienones in the case of butadiene and Z isomers in the case of isoprene.
Acylamidation of conjugated dienes
Gridnev, I. D.,Balenlova, E. S.
, p. 37 - 39 (2007/10/02)
The reaction of 1,3-butadiene and isoprene with complexes of acylium salts and nitriles takes place regiospecifically as 1,2-addition of acyl group and the nitrile at the double bond of the diene and leads to 4-vinyl-substituted 6-fluoro-5,6-dihydro-1,3-oxazines.Hydrolysis of the latter leads to unsaturated β-amino ketones.
