71371-92-1Relevant articles and documents
Photochemistry of Aminoketones. IV. Synthesis of 3-Aryl-pyrrolidinols-(3) via Photocyclization of β-Amino-propiophenones
Henning, H.-G.,Dietzsch, Th.,Fuhrmann, J.
, p. 435 - 444 (2007/10/02)
Photolysis (λirr>=300nm) of N-benzyl-N-benzoyl-β-aminopropiophenones 6-9 in abs. ether affords a 47-50percent yield of N-benzoyl-pyrrolidinols 12-18.The relative configurations of the diastereomeric 12-18 are determined by 1H-n.m.r. spectroscopy.The different behaviour of the N-acylated 6-9 in contrast to N,N-dialkyl-β-aminopropiophenones is explained by assumption of a dipol-dipol interaction between the keto and the amido carbonylgroups in the n,?*-excited state.