Cyanide ion promoted addition of acyl phosphonates to ethyl cyanoformate: synthesis of tertiary carbinols via tandem carbon-carbon bond formations |
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Authors: | Demir Ayhan S Reis Barbaros Reis Omer Eymür Serkan Göllü Mehmet Tural Servet Saglam Gülüzar |
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Institution: | Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey. asdemir@metu.edu.tr |
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Abstract: | New cyanation/phosphonate-phosphate rearrangement/C-acylation reactions of cyanophosphate anion with cyanoformate esters are described. Phase-transfer cocatalysts facilitate cyanide-catalyzed reactions between acyl phosphonates and cyanoformates to afford protected tertiary carbinol products in good to excellent yields (74-95%). Ethyl cyanoformate is used as a cyanide source and electrophile. The scope of the reaction was investigated by using a number of benzoyl and acyl phosphonates along with ethyl cyanoformate. Representative chemoselective reduction of the product 5a afforded ethyl 3-amino-2-hydroxy-2-phenylpropanoate (13) in good yield. |
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