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Beilstein J. Org. Chem. 2012, 8, 1091–1097, doi:10.3762/bjoc.8.120
Graphical Abstract
Figure 1: Representative isoindolinone natural products and pharmaceuticals.
Scheme 1: Formation of isomerized azepinoisoindoline 3 and oxirane 5.
Figure 2: X-Ray structure of epoxide 5.
Figure 3: Relative energies of alkene isomers based on RB3LYP/6-311G* calculations with MacSpartan ’06.
Scheme 2: Ring-closing metathesis of diene 2 in the absence of Ti(OiPr)4 and isolation of hydroxy epoxide 6 a...
Figure 4: X-Ray structure of epoxyalcohol 6.
Scheme 3: Preparation and RCM reaction of bis-terminal diene analogue 7.
Scheme 4: Conversion of epoxide 5 to 1,2-amino alcohols.
Figure 5: Amine building blocks for library synthesis.
Figure 6: X-ray structure of amino alcohol 10{7}.