Cyanide ion promoted addition of acyl phosphonates to ethyl cyanoformate:: Synthesis of tertiary carbinols via tandem carbon-carbon bond formations
Cyanide ion promoted addition of acyl phosphonates to ethyl cyanoformate:: Synthesis of tertiary carbinols via tandem carbon-carbon bond formations
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DOI：
10.1021/jo0710073
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发表时间：
2007-09-14
影响因子：
3.6
通讯作者：
Saglam, Gueluezar
中科院分区：
文献类型：
--
作者：
Demir, Ayhan S.;Reis, Barbaros;Saglam, Gueluezar
[GRAPHICS]New cyanation/phosphonate -phosphate rearrangement/Cacylation reactions of cyartophosphate 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- iydroxy-2-phenylpropanoate (13) in good yield.
