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Enantioselective ?-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from ?-Cyanoaldehydes.

ABSTRACT: The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective ?-cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology has also been applied to the total synthesis of the lignan natural product (-)-bursehernin.

SUBMITTER: Welin ER

PROVIDER: S-EPMC4548807 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

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Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes.

Welin Eric R ER Warkentin Alexander A AA Conrad Jay C JC MacMillan David W C DW

Angewandte Chemie (International ed. in English) 20150630 33

The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α-cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology has also been applied to the total synthesis of the lignan natural product (-)-bursehernin. ...[more]

PMID: 26130043

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