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. 2015 Aug 10;54(33):9668-72.
doi: 10.1002/anie.201503789. Epub 2015 Jun 30.

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

Eric R Welin  1 , Alexander A Warkentin  1 , Jay C Conrad  1 , David W C MacMillan  2
Affiliations

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

Eric R Welin et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: aldehydes; alkylation; organocatalysis; photoredox catalysis; total synthesis.

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Figures

Figure 1
Figure 1
Photoredox Organocatalysis α-Cyanoalkylation of Aldehydes.
Scheme 1
Scheme 1
Catalytic Cycle for Aldehyde α-Cyanoalkylation.
Scheme 2
Scheme 2
Total Synthesis of (−)-Bursehernin.
See this image and copyright information in PMC

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