Cyanide Ion Promoted Addition of Acylphosphonates to Diethyl Cyanophosphonate: Synthesis of Phosphonocyanohydrin O-Phosphates

被引：8

作者：

Demir, Ayhan S. ^{[1
]}

Aybey, Asuman ^{[1
]}

Emrullahoglu, Mustafa ^{[1
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

来源：

SYNTHESIS-STUTTGART | 2009年 / 10期

关键词：

phosphonocyanohydrins; diethyl cyanophosphonate; addition reactions; acyl phosphonates; nucleophilic additions; ACYL ANION EQUIVALENTS; CARBONYL-COMPOUNDS; BINOLAM-ALCL; PHOSPHORYLATION; REARRANGEMENT; PHOSPHONATES; CONVERSION; NITRILES; CATALYST; COMPLEX;

D O I：

10.1055/s-0029-1216634

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyanide ion catalyzed addition of acylphosphonates to diethyl cyanophosphonate furnished phosphonocyanohydrin O-phosphates in high yield. The reaction works via the phosphonate-phosphate rearrangement, followed by the addition of diethyl cyanophosphonate to the cyanohydrin phosphate anion.

引用

页码：1655 / 1658

页数：4

共 22 条

[1] Catalytic asymmetric cyano-phosphorylation of aldehydes promoted by heterobimetallic YLi3tris(binaphthoxide) (YLB) complex [J].

Abiko, Y ;

Yamagiwa, N ;

Sugita, M ;

Tian, J ;

Matsunaga, S ;

Shibasaki, M .

SYNLETT, 2004, (13) :2434-2436

[2] Solvent-free synthesis of racemic cyanohydrin O-phosphates [J].

Baeza, A ;

Nájera, C ;

Sansano, JM .

ARKIVOC, 2005, :353-363

[3] Binolam-AlCl:: A two-centre catalyst for the synthesis of enantioenriched cyanohydrin O-phosphates [J].

Baeza, A ;

Nájera, C ;

Sansano, JM ;

Saá, JM .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (13) :3849-3862

[4] Enantioselective synthesis of cyanohydrin O-phosphates mediated by the bifunctional catalyst binolam-AlCl [J].

Baeza, A ;

Casas, J ;

Nájera, C ;

Sansano, JM ;

Saá, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (27) :3143-3146

[5] Generation of acyl anion equivalents from acylphosphonates via phosphonate-phosphate rearrangement:: A highly practical method for cross-benzoin reaction [J].

Demir, AS ;

Reis, Ö ;

Igdir, AÇ ;

Esiringü, I ;

Eymur, S .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (25) :10584-10587

[6] Addition of trifluoromethyltrimethylsilane to acyl phosphonates: Synthesis of TMS-Protected 1-alkyl-1-trifluoromethyl-1-hydroxyphosphonates and 1-aryldifluoroethenyl phosphates [J].

Demir, Ayhan S. ;

Eymur, Serkan .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8527-8530

[7] Uncatalyzed addition of TMSCN to acylphosphonates [J].

Demir, Ayhan S. ;

Reis, Omer ;

Kayalar, Metin ;

Eymur, Serkan ;

Reis, Barbaros .

SYNLETT, 2006, (19) :3329-3333

[8] Protonation of acyl anion equivalents generated from acylphosphonates:: nonhydride access to the aldehyde oxidation state from the carboxylic acid oxidation state [J].

Demir, Ayhan S. ;

Reis, Omer ;

Esiringu, Ilker ;

Reis, Barbaros ;

Baris, Sehriban .

TETRAHEDRON, 2007, 63 (01) :160-165

[9] Cyanide ion promoted addition of acyl phosphonates to ethyl cyanoformate:: Synthesis of tertiary carbinols via tandem carbon-carbon bond formations [J].

Demir, Ayhan S. ;

Reis, Barbaros ;

Reis, Omer ;

Eymuer, Serkan ;

Goellue, Mehmet ;

Tural, Servet ;

Saglam, Gueluezar .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) :7439-7442

[10] Cyano-phosphorylation of aldehydes catalyzed by a nucleophilic N-heterocyclic carbene [J].

Fukuda, Y ;

Maeda, Y ;

Kondo, K ;

Aoyama, T .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (03) :397-398

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