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Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)-Catalyzed C-H Alkylation of Azacycles.

ABSTRACT: The development of new and practical 3-pentoxythiocarbonyl auxiliaries for IrI -catalyzed C-H alkylation of azacycles is described. This method allows for the ?-C-H alkylation of a variety of substituted pyrrolidines, piperidines, and tetrahydroisoquinolines through alkylation with alkenes. While the practicality of these simple carbamate-type auxiliaries is underscored by the ease of installation and removal, the method's utility is demonstrated in its ability to functionalize biologically relevant l-proline and l-trans-hydroxyproline, delivering unique 2,5-dialkylated amino acid analogues that are not accessible by other C-H functionalization methods.

SUBMITTER: Tran AT

PROVIDER: S-EPMC5561469 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)-Catalyzed C-H Alkylation of Azacycles.

Tran Anh T AT Yu Jin-Quan JQ

Angewandte Chemie (International ed. in English) 20170724 35

The development of new and practical 3-pentoxythiocarbonyl auxiliaries for IrI -catalyzed C-H alkylation of azacycles is described. This method allows for the α-C-H alkylation of a variety of substituted pyrrolidines, piperidines, and tetrahydroisoquinolines through alkylation with alkenes. While the practicality of these simple carbamate-type auxiliaries is underscored by the ease of installation and removal, the method's utility is demonstrated in its ability to functionalize biolog ...[more]

PMID: 28620981

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