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- W2133086016 abstract "A versatile, robust, and stereocomplementary synthesis of fully-substituted (E)- and (Z)-stereodefined α,β-unsaturated esters 3 from accessible α-substituted β-ketoesters 1via (E)- and (Z)-enol phosphonates was achieved. The present method involves two accessible reaction sequences: (i) (E)- and (Z)-stereocomplementary enol phosphorylations of a wide variety of β-ketoesters 1 (24 examples; 71–99% yield, each >95: 5 ds), and (ii) (E)- and (Z)-stereoretentive Suzuki–Miyaura cross-coupling (16 examples; 71–91% yield, >81/19 ds) and Negishi cross-coupling (32 examples; 65–96% yield, >95 : 5 ds) using (E)- and (Z)-enol phosphonates 2. 1H-NMR monitoring for a key reactive N-phosphorylammonium (imidazolium) intermediate I and an application in the synthesis of both (E)- and (Z)-tamoxifen precursors 6 are described." @default.
- W2133086016 created "2016-06-24" @default.
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- W2133086016 date "2015-01-01" @default.
- W2133086016 modified "2023-10-08" @default.
- W2133086016 title "(E)- and (Z)-stereodefined enol phosphonates derived from β-ketoesters: stereocomplementary synthesis of fully-substituted α,β-unsaturated esters" @default.
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- W2133086016 doi "https://doi.org/10.1039/c5ob01097g" @default.
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