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Issue 25, 2012
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Synthesis and evaluation of atropos dihydro-5H-dibenzazepinium halide PTCs derived from α-methylbenzylamine

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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.

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

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Supplementary files

Article information


Submitted
28 Feb 2012
Accepted
09 May 2012
First published
22 May 2012

Org. Biomol. Chem., 2012,10, 4968-4976
Article type
Paper

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

B. Lygo, U. Butt and M. Cormack, Org. Biomol. Chem., 2012, 10, 4968 DOI: 10.1039/C2OB25437A

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