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Synthesis of Pyrrolidines and Pyrroles via Tandem Amination/Cyanation/Alkylation and Amination/Oxidation Sequences.

ABSTRACT: Starting from a primary amine-tethered alkyne 1, a copper-catalyzed three-component tandem amination/cyanation/alkylation sequence gives ?-CN pyrrolidine 6 in good yield and regioselectivity. Also, a silver mediated tandem amination/oxidation of a secondary amine-tethered alkyne 7 produces functionalized pyrrole 8 in good yield. All reactions were conducted in one pot without any protection/deprotection steps.

SUBMITTER: Han J

PROVIDER: S-EPMC4224302 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Synthesis of Pyrrolidines and Pyrroles via Tandem Amination/Cyanation/Alkylation and Amination/Oxidation Sequences.

Han Junbin J Lu Zhichao Z Hammond Gerald B GB Xu Bo B

European journal of organic chemistry 20140901 26

Starting from a primary amine-tethered alkyne 1, a copper-catalyzed three-component tandem amination/cyanation/alkylation sequence gives α-CN pyrrolidine 6 in good yield and regioselectivity. Also, a silver mediated tandem amination/oxidation of a secondary amine-tethered alkyne 7 produces functionalized pyrrole 8 in good yield. All reactions were conducted in one pot without any protection/deprotection steps. ...[more]

PMID: 25386099

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