期刊
ACS CATALYSIS
卷 8, 期 2, 页码 1062-1066出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03788
关键词
asymmetric catalysis; organocatalysis; iminium ion; photochemistry; radical reactivity
资金
- Generalitat de Catalunya (CERCA Program)
- Agencia Estatal de Investigacion (AEI) [CTQ2016-75520-P]
- Agencia Estatal de Investigacion (AEI) (Severo Ochoa Excellence Accreditation) [SEV-2013-0319]
- European Research Council [ERC-2015-CoG 681840 - CATA-LUX]
- Marie Sklodowska-Curie Actions [H2020-MSCA-IF-2014 658980]
- MINECO [CTQ2013-45938-P]
- H-MSCA-ITN [722591 - PHOTOTRAIN]
The direct introduction of sp(3) carbon fragments at the beta position of a,beta-unsaturated aldehydes is greatly complicated by competing 1,2-addition manifolds. Previous catalytic enantioselective conjugate addition methods, based on the use of organometallic reagents or ground-state iminium ion activation, could not provide general and efficient solutions. We report herein that, by turning them into strong oxidants, visible light excitation of chiral iminium ions triggers a stereocontrolled radical pathway that exclusively affords highly enantioenriched beta-substituted aldehydes bearing a variety of alkyl fragments.
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