One-pot stereoselective synthesis of ?,?-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular SN2 reaction.
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ABSTRACT: We report here an efficient one-pot method for the synthesis of ?,?-differentiated diamino esters directly from cinnamate esters using N,N-dichloro-p-toluenesulfonamide and benzylamine as nitrogen sources. The key transformations include a Cu-catalyzed aminohalogenation and aziridination, followed by an intermolecular SN2 nucleophilic ring opening by benzylamine. The reactions feature a wide scope of substrates and proceed with excellent stereo- and regioselectivity (anti:syn >99:1) .
SUBMITTER: Xiong Y
PROVIDER: S-EPMC4142878 | biostudies-literature | 2014
REPOSITORIES: biostudies-literature
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