Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 31, Pages 11521-11524Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja406181e
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Funding
- NIGMS [R01 GM-093213-03]
- German Academic Exchange Service (DAAD)
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The direct, asymmetric alpha-amination of aldehydes has been accomplished via a combination of photoredox and organocatalysis. Photon-generated N-centered radicals undergo enantioselective alpha-addition to catalytically formed chiral enamines to directly produce stable alpha-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 alpha-amino aldehyde products that do not require postreaction manipulation.
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