Bridged [3.3.1]-bisaminal structures, namely 6,12-epiminodibenzo[,][1,5]diazocines, are herein named McGeachin-type bisaminals. The TsOH-catalyzed chiral synthesis of McGeachin-type bisaminals is first developed by condensation of two molecules of 2-(methylamino)benzaldehyde and one molecule of chiral amines. Two chiral diastereomers are generated simultaneously and are isolated by column chromatography in a total yield of up to 99%. The absolute structure of one stereoisomer was determined by X-ray crystallography.
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| http://dx.doi.org/10.1021/acs.joc.9b03362 | DOI Listing |
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