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New strategy for the synthesis of substituted morpholines.

ABSTRACT: 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.

SUBMITTER: Leathen ML

PROVIDER: S-EPMC2709957 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature

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New strategy for the synthesis of substituted morpholines.

Leathen Matthew L ML Rosen Brandon R BR Wolfe John P JP

The Journal of organic chemistry 20090701 14

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. ...[more]

PMID: 19480462

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