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- W2898248422 endingPage "1524" @default.
- W2898248422 startingPage "1515" @default.
- W2898248422 abstract "Abstract Asymmetric 1,2‐additions of cyanide yield enantioenriched cyanohydrins as versatile chiral building blocks. Next to HCN, volatile organic cyanide sources are usually used. Among them, cyanoformates are more attractive on technical scale than TMSCN for cost reasons, but catalytic productivity is usually lower. Here, the development of a new strategy for cyanations is described, in which this activity disadvantage is overcome. A Lewis acidic Al center cooperates with an aprotic onium moiety within a remarkably robust bifunctional Al–F–salen complex. This allowed for unprecedented turnover numbers of up to 10 4 . DFT studies suggest an unexpected unique trimolecular pathway in which the ammonium bound cyanide attacks the aldehyde, which itself is activated by the carbonyl group of the cyanoformate binding to the Al center. In addition, a novel practical carboxycyanation method was developed that makes use of KCN as the sole cyanide source. The use of a pyrocarbonate as carboxylating reagent provided the best results." @default.
- W2898248422 created "2018-11-02" @default.
- W2898248422 creator A5000025617 @default.
- W2898248422 creator A5000460023 @default.
- W2898248422 creator A5018244791 @default.
- W2898248422 creator A5056979833 @default.
- W2898248422 creator A5063493171 @default.
- W2898248422 creator A5064547750 @default.
- W2898248422 creator A5068922206 @default.
- W2898248422 creator A5069980959 @default.
- W2898248422 creator A5090471164 @default.
- W2898248422 date "2019-01-02" @default.
- W2898248422 modified "2023-10-15" @default.
- W2898248422 title "Asymmetric Carboxycyanation of Aldehydes by Cooperative AlF/Onium Salt Catalysts: from Cyanoformate to KCN as Cyanide Source" @default.
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