Organic & Biomolecular Chemistry 2012-07-07

Synthesis and evaluation of atropos dihydro-5H-dibenzazepinium halide PTCs derived from α-methylbenzylamine.

Barry Lygo, Umar Butt, Maria Cormack

Index: Org. Biomol. Chem. 10(25) , 4968-76, (2012)

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Abstract

A short synthetic route to diastereoisomeric atropos dihydro-5H-dibenz[c,e]azepinium salts via reaction of a single enantiomer of (R)-α-methylbenzylamine with a racemic atropos biphenol derivative is described. Compounds prepared via this approach are used to provide strong evidence that structurally related tropos dihydro-5H-dibenz[c,e]azepinium salts preferentially react via a single conformation in PTC reactions involving glycine imine enolates.