952514-97-5Relevant academic research and scientific papers
Cyanide ion promoted addition of acyl phosphonates to ethyl cyanoformate: Synthesis of tertiary carbinols via tandem carbon-carbon bond formations
Demir, Ayhan S.,Reis, Barbaros,Reis, Oemer,Eymuer, Serkan,Goellue, Mehmet,Tural, Servet,Saglam, Gueluezar
, p. 7439 - 7442 (2007)
(Chemical Equation Presented) 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.
