Abstract
Herein, we report a general iminium ion-based catalytic method for the enantioselective conjugate addition of carbon-centered radicals to aliphatic and aromatic enals. The process uses an organic photoredox catalyst, which absorbs blue light to generate radicals from stable precursors, in combination with a chiral amine catalyst, which secures a consistently high level of stereoselectivity. The generality of this catalytic platform is demonstrated by the stereoselective interception of a wide variety of radicals, including non-stabilized primary ones which are generally difficult to engage in asymmetric processes. The system also served to develop organocatalytic cascade reactions that combine an iminium-ion-based radical trap with an enamine-mediated step, affording stereochemically dense chiral products in one-step.
Original language | English |
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Pages (from-to) | 5357-5362 |
Number of pages | 6 |
Journal | Angewandte Chemie - International Edition |
Volume | 60 |
Issue number | 10 |
DOIs | |
State | Published - 1 Mar 2021 |
Externally published | Yes |
Keywords
- asymmetric catalysis
- cascade reactions
- organocatalysis
- photoredox catalysis
- radical chemistry
ASJC Scopus subject areas
- Catalysis
- General Chemistry