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

被引：82

作者：

Demir, AS ^{[1
]}

Reis, Ö ^{[1
]}

Igdir, AÇ ^{[1
]}

Esiringü, I ^{[1
]}

Eymur, S ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 25期

关键词：

D O I：

10.1021/jo051811u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acylphosphonates are potent acyl anion precursors that generate acyl anion equivalents under the promotion of cyanide anion via phosphonate-phosphate rearrangement. These anions readily react with aldehydes to provide cross-benzoin products. In this way it is possible to synthesize a variety of aromatic-aromatic, aromatic-aliphatic, and aliphatic-aromatic benzoins. Moreover the reaction of benzoylphosphonate with potent electrophile 2,2,2-trifluoroacetophenone provided the corresponding aldehyde-ketone coupling product in high yield.

引用

页码：10584 / 10587

页数：4

共 36 条

[1] Cyanide-catalyzed additions of acyl phosphonates to aldehydes: A new acyl donor for benzoin-type reactions [J].

Bausch, CC ;

Johnson, JS .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (09) :1207-1211

[2] REACTIONS OF AROYL HALIDES WITH PHOSPHITES . ESTERS OF AROYLPHOSPHONIC ACIDS [J].

BERLIN, KD ;

TAYLOR, HA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (18) :3862-&

[3] SOME MOLECULAR-REARRANGEMENTS OF ORGANOSILICON COMPOUNDS [J].

BROOK, AG .

ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (03) :77-84

[4] Efficient synthesis of acylsilanes using morpholine amides [J].

Clark, CT ;

Milgram, BC ;

Scheidt, KA .

ORGANIC LETTERS, 2004, 6 (22) :3977-3980

[5] A highly enantio- and diastereoselective catalytic intramolecular stetter reaction [J].

de Alaniz, JR ;

Rovis, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6284-6289

[6]

DEGL'INNOCENTI A, 1987, GAZZ CHIM ITAL, V117, P645

[7] A convenient and selective synthesis of unsymmetrical benzoins via the cyanide ion catalyzed cleavage of benzils [J].

Demir, AS ;

Reis, Ö .

TETRAHEDRON, 2004, 60 (17) :3803-3811

[8] Development of a donor-acceptor concept for enzymatic cross-coupling reactions of aldehydes:: The first asymmetric cross-benzoin condensation [J].

Dünkelmann, P ;

Kolter-Jung, D ;

Nitsche, A ;

Demir, AS ;

Siegert, P ;

Lingen, B ;

Baumann, M ;

Pohl, M ;

Müller, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (41) :12084-12085

[9] Thiazol-2-ylidene catalysis in intramolecular crossed aldehyde-ketone benzoin reactions [J].

Enders, D ;

Niemeier, O .

SYNLETT, 2004, (12) :2111-2114

[10] Nucleophilic carbenes in asymmetric organocatalysis [J].

Enders, D ;

Balensiefer, T .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :534-541

← 1 2 3 4 →