Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 19, Pages 6120-6123Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b01662
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Funding
- ICIQ Foundation
- MICINN [CTQ2013-45938-P]
- European Research Council [ERC 278541-ORGA-NAUT]
- MINECO through the Severo Ochoa Excellence Accreditation [SEV-2013-0319]
- ICREA Funding Source: Custom
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Disclosed herein is a photo-organocatalytic enantioselective alpha- and gamma-alkylation of aldehydes and enals, respectively, with bromomalonates. The chemistry uses a Commercially available aminocatalyst and occurs under Illumination by a fluorescent light bulb in the absence of any external photoredox catalyst. Mechanistic investigations reveal the previously hidden ability of transiently generated enamines to directly reach an electronically excited state upon light absorption while successively triggering the formation of reactive radical species from the organic halides. At the same time, the ground state chiral enamines provide effective stereochemical induction for the enantioselective alkylation process.
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