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- W4200216503 abstract "The access towards chiral nitriles remains crucial in the synthesis of several pharmaceuticals. One approach is based on metal-catalyzed dehydration of chiral aldoximes, which are generated from chiral pool-derived aldehydes as substrates, and the use of a cheap and readily available nitrile as co-substrate and water acceptor. Dehydration of N-acyl α-amino aldoximes such as N-Boc-l-prolinal oxime catalyzed by copper(II) acetate provides access to the corresponding N-acyl α-amino nitriles, which are substructures of the pharmaceuticals Vildagliptin and Saxagliptin. In this work, a detailed investigation of the formation of the amide as a by-product at higher substrate loadings is performed. The amide formation depends on the electronic properties of the nitrile co-substrate. We could identify an acceptor nitrile which completely suppressed amide formation at high substrate loadings of 0.5 m even when being used with only 2 equivalents. In detail, utilization of trichloroacetonitrile as such an acceptor nitrile enabled the synthesis of N-Boc-cyanopyrrolidine in a high yield of 92 % and with full retention of the absolute configuration." @default.
- W4200216503 created "2021-12-31" @default.
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- W4200216503 date "2021-12-10" @default.
- W4200216503 modified "2023-10-16" @default.
- W4200216503 title "Process Development of the Copper(II)‐Catalyzed Dehydration of a Chiral Aldoxime and Rational Selection of the Co‐Substrate" @default.
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- W4200216503 doi "https://doi.org/10.1002/open.202100230" @default.
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