Mandelic acid as synthetic equivalent of benzoyl carbanion.: Synthesis of nitrobenzophenones

被引：7

作者：

Blay, G ^{[1
]}

Cardona, L ^{[1
]}

Fernández, I ^{[1
]}

Michelena, R ^{[1
]}

Pedro, JR ^{[1
]}

Ramírez, T ^{[1
]}

Ruiz-García, R ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain

来源：

SYNLETT | 2003年 / 15期

关键词：

acetals; nucleophilic aromatic substitutions; ketones; oxygen; oxidations; decarboxylation;

D O I：

10.1055/s-2003-42123

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrobenzophenones are prepared from a mandelic acid dioxolanone. The sequence starts with the aromatic nucleophilic substitution of the enolate of the dioxolanone onto p-fluoronitrobenzenes, followed by hydrolysis of the acetal moiety and oxidative decarboxylation of the resulting alpha-hydroxyacids. The whole sequence involves the use of mandelic acid as synthetic equivalent of the benzoyl carbanion.

引用

页码：2325 / 2328

页数：4

共 38 条

[1] Asymmetric arylation of ketone enolates
Ahman, J
Wolfe, JP
Troutman, MV
Palucki, M
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) : 1918 - 1919
[2] Highly diastereoselective Michael reaction of (S)-mandelic acid enolate.: Chiral benzoyl carbanion equivalent through an oxidative decarboxylation of α-hydroxyacids
Blay, G
Fernández, I
Monje, B
Pedro, JR
Ruiz, R
[J]. TETRAHEDRON LETTERS, 2002, 43 (47) : 8463 - 8466
[3] Nucleophilic benzoylation using lithiated methyl mandelate as a synthetic equivalent of the benzoyl carbanion.: Oxidative decarboxylation of α-hydroxyacids
Blay, G
Fernández, I
Formentin, P
Monje, B
Pedro, JR
Ruiz, R
[J]. TETRAHEDRON, 2001, 57 (06) : 1075 - 1081
[4] Catalytic aerobic oxidative decarboxylation of α-hydroxy-acids.: Methyl mandelate as a benzoyl anion equivalent
Blay, G
Fernández, B
Formentin, P
Pedro, JR
Roselló, AL
Ruiz, R
Journaux, Y
[J]. TETRAHEDRON LETTERS, 1998, 39 (20) : 3327 - 3330
[5] Bull DJ, 1996, SYNLETT, P647
[6] CONDENSATION OF AROMATIC NITRO COMPOUNDS WITH ARYLACETONITRILES .4. SOME REACTIONS OF ARYLCYANOMETHYLENEQUINONE OXIMES
DAVIS, RB
BENIGNI, JD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (05) : 1605 - &
[7] Synthesis of the benzophenone fragment of balanol via an intramolecular cyclization event
Denieul, MP
Laursen, B
Hazell, R
Skrydstrup, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) : 6052 - 6060
[8] DURST T, 1980, COMPREHENSIVE CARB A, pCH5
[9] Freund R, 2000, HELV CHIM ACTA, V83, P1247, DOI 10.1002/1522-2675(20000607)83:6<1247::AID-HLCA1247>3.0.CO
[10] 2-1

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