929688-03-9Relevant academic research and scientific papers
Novel synthesis of naturally occurring pulvinones: A heck coupling, transesterification, and Dieckmann condensation strategy
Bernier, David,Brueckner, Reinhard
, p. 2249 - 2272 (2008/03/12)
Phosphine-free Heck alkenylations of iodoarenes with trifluoroethyl 2-acetoxyacrylate (19) led stereoselectively to trifluoroethyl (Z)-2-acetoxycinnamates 31-34, 42, 44, and 51. Deacetylation followed by acylation with N,N′-dicyclohexylcarbodiimide activa
Tandem Claisen condensation/transesterification between arylacetate enolates and arylmethylene-substituted 2,2-dimethyl-1,3-dioxolan-4-ones: An improved synthesis of z-configured pulvinones
Kaczybura, Natasza,Brueckner, Reinhard
, p. 118 - 130 (2007/12/26)
Horner-Wadsworth-Emmons (HWE) alkenations of aromatic aldehydes with the novel phosphonate 24b led to E-configured arylmethylene-substituted 2,2-dimethyl-1,3-dioxolan-4-ones 25a-f (79-88% yield). The latter condensed with the lithium enolates of methyl arylacetates lithio-20b-d to give, after acid treatment and crystallization, isomerically pure (Z)-pulvinones 8d-s in 75-91% yield. We also showed that Horner-Wadsworth-Emmons reactions between phosphonate 24b and aliphatic aldehydes lead to E-configured alkylmethylene-substituted 2,2-dimethyl-1,3-dioxolan-4-ones 25g-i (82-96% yield). Georg Thieme Verlag Stuttgart.
