Brandon Rosen - New Strategy for the Synthesis of Substituted Morpholines

Document created by Brandon Rosen on Aug 22, 2014
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  Publication Details (including relevant citation   information):

  Leathen, M. L.; Rosen, B. R.; Wolfe, J. P. J. Org. Chem. 2009,   74, 5107.


  A four-step synthesis of cis-3,5-disubstituted   morpholines from enantiomerically pure amino alcohols is   described. The key step in the synthesis is a Pd-catalyzed   carboamination reaction between a substituted ethanolamine   derivative and an aryl or alkenyl bromide. The morpholine   products are generated as single stereoisomers in moderate to   good yield. This strategy also provides access to fused bicyclic   morpholines as well as 2,3- and 2,5-disubstituted products.

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