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Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N-Acyliminium Ions
| Title: | Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N-Acyliminium Ions |
| Authors: | Grossmann, Oleg Browse this author | | Maji, Rajat Browse this author | | Aukland, Miles H. Browse this author | | Lee, Sunggi Browse this author | | List, Benjamin Browse this author →KAKEN DB |
| Keywords: | Lewis acids | | N-acyliminium ions | | Mukaiyama-Mannich reaction | | imidodiphosphorimidates | | organocatalysis |
| Issue Date: | 21-Feb-2022 |
| Publisher: | Wiley-Blackwell |
| Journal Title: | Angewandte chemie-international edition |
| Volume: | 61 |
| Issue: | 9 |
| Start Page: | e202115036 |
| Publisher DOI: | 10.1002/anie.202115036 |
| Abstract: | Strong and confined imidodiphosphorimidate (IDPi) catalysts enable highly enantioselective substitutions of cyclic, aliphatic hemiaminal ethers with enol silanes. 2-Substituted pyrrolidines, piperidines, and azepanes are obtained with high enantioselectivities, and the method displays a broad tolerance of various enol silane nucleophiles. Several natural products can be accessed using this methodology. Mechanistic studies support the intermediacy of non-stabilized, cyclic N-(exo-acyl)iminium ions, paired with the confined chiral counteranion. Computational studies suggest transition states that explain the observed enantioselectivity. |
| Type: | article |
| URI: | http://hdl.handle.net/2115/85413 |
| Appears in Collections: | 化学反応創成研究拠点：ICReDD (Institute for Chemical Reaction Design and Discovery : ICReDD) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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