Enantioselective Giese Additions of Prochiral α-Amino Radicals.
In: Journal of the American Chemical Society, Jg. 144 (2022-12-14), Heft 49, S. 22451-22457
academicJournal
Zugriff:
Amines featuring an adjacent stereocenter are important building blocks, and recent years have seen remarkable growth in methods forming these via prochiral α-amino radical intermediates. However, very few can exert control over the newly formed stereocenter. We disclose a strategy to overcome this in the context of one of the most widely used radical carbon-carbon bond forming reactions, the Giese reaction. Incorporation of a removable basic heteroarene into the substrate enables a network of attractive noncovalent interactions between a phosphoric acid catalyst, the subsequently formed α-amino radical, and the Giese acceptor, allowing the catalyst to exert control during the C-C bond forming step. Deprotection of the products leads to analogues of γ-aminobutyric acid. We anticipate that this strategy will be applicable to other asymmetric radical transformations in which catalyst control is presently challenging.
Titel: |
Enantioselective Giese Additions of Prochiral α-Amino Radicals.
|
---|---|
Autor/in / Beteiligte Person: | Lahdenperä, ASK ; Bacoş, PD ; Phipps, RJ |
Zeitschrift: | Journal of the American Chemical Society, Jg. 144 (2022-12-14), Heft 49, S. 22451-22457 |
Veröffentlichung: | Washington, DC : American Chemical Society ; <i>Original Publication</i>: Easton, Pa. [etc.], 2022 |
Medientyp: | academicJournal |
ISSN: | 1520-5126 (electronic) |
DOI: | 10.1021/jacs.2c11367 |
Schlagwort: |
|
Sonstiges: |
|