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One-pot stereoselective synthesis of ?,?-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular SN2 reaction.

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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One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular SN2 reaction.

Xiong Yiwen Y Qian Ping P Cao Chenhui C Mei Haibo H Han Jianlin J Li Guigen G Pan Yi Y

Beilstein journal of organic chemistry 20140807

We report here an efficient one-pot method for the synthesis of α,β-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) . ...[more]

PMID: 25161740

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