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Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.

ABSTRACT: We report a highly enantioselective Pd-PHOX-catalyzed intermolecular hydroalkylation of acyclic 1,3-dienes. Meldrum's acid derivatives and other activated C-pronucleophiles, such as ?-diketones and malononitriles, react with a variety of aryl- and alkyl-substituted dienes in ?20 h at room temperature. The coupled products, obtained in up to 96% yield and 97.5:2.5 er, are easily transformed into useful chemical building blocks for downstream synthesis.

SUBMITTER: Adamson NJ 

PROVIDER: S-EPMC5937024 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.

Adamson Nathan J NJ   Wilbur Katherine C E KCE   Malcolmson Steven J SJ  

Journal of the American Chemical Society 20180220 8

We report a highly enantioselective Pd-PHOX-catalyzed intermolecular hydroalkylation of acyclic 1,3-dienes. Meldrum's acid derivatives and other activated C-pronucleophiles, such as β-diketones and malononitriles, react with a variety of aryl- and alkyl-substituted dienes in ≤20 h at room temperature. The coupled products, obtained in up to 96% yield and 97.5:2.5 er, are easily transformed into useful chemical building blocks for downstream synthesis. ...[more]

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