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Enantioselective direct ?-amination of aldehydes via a photoredox mechanism: a strategy for asymmetric amine fragment coupling.

ABSTRACT: The direct, asymmetric ?-amination of aldehydes has been accomplished via a combination of photoredox and organocatalysis. Photon-generated N-centered radicals undergo enantioselective ?-addition to catalytically formed chiral enamines to directly produce stable ?-amino aldehyde adducts bearing synthetically useful amine substitution patterns. Incorporation of a photolabile group on the amine precursor obviates the need to employ a photoredox catalyst in this transformation. Importantly, this photoinduced transformation allows direct and enantioselective access to ?-amino aldehyde products that do not require postreaction manipulation.

SUBMITTER: Cecere G

PROVIDER: S-EPMC3786402 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature

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Enantioselective direct α-amination of aldehydes via a photoredox mechanism: a strategy for asymmetric amine fragment coupling.

Cecere Giuseppe G König Christian M CM Alleva Jennifer L JL MacMillan David W C DW

Journal of the American Chemical Society 20130726 31

The direct, asymmetric α-amination of aldehydes has been accomplished via a combination of photoredox and organocatalysis. Photon-generated N-centered radicals undergo enantioselective α-addition to catalytically formed chiral enamines to directly produce stable α-amino aldehyde adducts bearing synthetically useful amine substitution patterns. Incorporation of a photolabile group on the amine precursor obviates the need to employ a photoredox catalyst in this transformation. Importantly, this ph ...[more]

PMID: 23869694

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