Direct and enantioselective aldol reactions catalyzed by chiral nickel(II) complexes
| Autor: | Stuart C. D. Kennington, Mercè Font-Bardia, Miguel Mellado-Hidalgo, Sabrina Puddu, Saul F. Teloxa, Gabriel Aullón, Oriol Galeote, Marina Bellido, Pedro Romea, Fèlix Urpí |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Níquel
chemistry.chemical_element thiazinanethiones Asymmetric Catalysis | Hot Paper direct reaction 010402 general chemistry 01 natural sciences Catalysis Adduct nickel Aldol reaction Nickel Atom economy polycyclic compounds aldol reaction 010405 organic chemistry Communication organic chemicals Síntesi asimètrica Enantioselective synthesis asymmetric catalysis Asymmetric synthesis General Medicine General Chemistry Combinatorial chemistry Communications 0104 chemical sciences chemistry Reacció aldòlica Direct reaction |
| Zdroj: | Dipòsit Digital de la UB Universidad de Barcelona Angewandte Chemie (International Ed. in English) |
| Popis: | A direct and asymmetric aldol reaction of N‐acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes is reported. The reaction gives the corresponding O‐TIPS‐protected anti‐aldol adducts in high yields and with remarkable stereocontrol and atom economy. Furthermore, the straightforward removal of the achiral scaffold provides enantiomerically pure intermediates of synthetic interest, which involve precursors for anti‐α‐amino‐β‐hydroxy and α,β‐dihydroxy carboxylic derivatives. Theoretical calculations explain the observed high stereocontrol. Appropriate and simultaneous activation of robust and easy to handle [Tol‐BINAP]NiCl2 and aromatic aldehydes with TIPSOTf orchestrates a direct, asymmetric, and catalytic aldol reaction of a wide array of N‐acyl‐1,3‐thiazinane‐2‐thiones. This method enables the corresponding TIPS‐protected anti aldol adducts to be obtained in a highly efficient and atom economical manner. |
| Databáze: | OpenAIRE |
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