0000000000214960
AUTHOR
Tímea Gonda
Stereoselective synthesis and application of tridentate aminodiols derived from (+)-pulegone
Abstract A library of tridentate aminodiols, derived from naturally occurring (R)-(+)-pulegone, was synthesized and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The reduction of pulegone furnished pulegol, which was transformed into allylic trichloroacetamide via Overman rearrangement of the corresponding trichloroacetimidate. The protected enamine was subjected to dihydroxylation with OsO4/NMO system resulting in a 1:1 mixture of (1R,2R,4R)- and (1S,2S,4R)-aminodiol diastereomers. After the removal of the trichloroacetyl protecting groups, the obtained primary aminodiols were transformed into secondary ones. The regioselectivity of the ring closure of the N-b…
CCDC 1470051: Experimental Crystal Structure Determination
Related Article: Tímea Gonda, Zsolt Szakonyi, Antal Csámpai, Matti Haukka, Ferenc Fülöp|2016|Tetrahedron:Asymm.|27|480|doi:10.1016/j.tetasy.2016.04.009
CCDC 1470052: Experimental Crystal Structure Determination
Related Article: Tímea Gonda, Zsolt Szakonyi, Antal Csámpai, Matti Haukka, Ferenc Fülöp|2016|Tetrahedron:Asymm.|27|480|doi:10.1016/j.tetasy.2016.04.009