Stereochemistry of the Kabachnik-Fields Condensation of Terpenic Amino Oximes with Aldehydes and Dimethyl Phosphite

Результат исследования: Научные публикации в периодических изданияхстатья

Аннотация

Three-component condensation of aldehydes and dimethyl phosphite with α-amino oximes derived from (−)-α-pinene and (+)-3-carene (Kabachnik-Fields reaction) resulted in amino phosphonates as pairs of diastereomers. Diastereomeric ratio depends on the catalyst used (SnCl2×2H2O, SiO2, Al2O3-H+) and the heating type (conventional or microwave). The best results were achieved by MW irradiation with simultaneous cooling. Stereochemical assignment of the key derivatives was made by X-ray diffractometry. According to quantum chemical calculations (DFT PBE0/def2-TZVPP) and spectroscopic data, the terpenic α-amino phosphonates should be conformationally inhomogeneous, exhibiting a tendency to form H-bonded dimers (DFT M06/def2-SVP, IR). One-bond spin-spin coupling 1JP–C was found to be diagnostic for the configuration assignment since the value 1JP–C depends on the dihedral angle between bond C−P and axis of the electron lone pair at the neighboring nitrogen (NMR, DFT PBE0/aug-cc-pVTZ−J).

Язык оригиналаанглийский
Страницы (с-по)7596-7604
Число страниц9
ЖурналChemistrySelect
Том5
Номер выпуска25
DOI
СостояниеОпубликовано - 7 июл 2020

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