289666-59-7Relevant academic research and scientific papers
Enantioselective diels-alder reactions of chiral racemic acyclic dienes with (SS)-2-(p-tolylsulfinyl)-1,4-naphthoquinone
Carreno, M. Carmen,Garcia-Cerrada, Susana,Urbano, Antonio,Di Vitta, Claudio
, p. 2965 - 2969 (1998)
Enantiopure sulfinylnaphthoquinone (+)-1 reacted with racemic acyclic dienes 2a-f bearing a stereogenic allylic center, through a tandem cycloaddition/pyrolytic sulfenic acid elimination, to afford enantio-enriched compounds 4a-f and 5a-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.
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.
