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  • Title: Cyanide ion promoted addition of acyl phosphonates to ethyl cyanoformate: synthesis of tertiary carbinols via tandem carbon-carbon bond formations.
    Author: Demir AS, Reis B, Reis O, Eymür S, Göllü M, Tural S, Saglam G.
    Journal: J Org Chem; 2007 Sep 14; 72(19):7439-42. PubMed ID: 17715973.
    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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