C-C Coupling of Acyclic Nitronates with Silyl Ketene Acetals under Silyl Triflate Catalysis: Reactivity Umpolung of Aliphatic Nitro Compounds

被引：22

作者：

Smirnov, Vladimir O. ^{[1
]}

Khomutova, Yulia A. ^{[1
]}

Tartakovsky, Vladimir A. ^{[1
]}

Ioffe, Sema L. ^{[1
]}

机构：

[1] ND Zelinskii Inst Organ Chem, Moscow 119991, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 18期

基金：

俄罗斯基础研究基金会;

关键词：

Umpolung; C-C coupling; Nitro compounds; Hydrogenation; Amino-; acids; MULTICOMPONENT REACTION; ACID; CONVERSION; CHEMISTRY; TANDEM; ESTERS; ROUTE; NEF;

D O I：

10.1002/ejoc.201200239

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

TBSOTf-promoted C-C coupling of alkyl and trialkylsilyl nitronates with silyl ketene acetals yields functionalized nitroso acetals. This conversion may serve as a new simple procedure to reverse the conventional reactivity of aliphatic nitro compounds. Preliminary results on the hydrogenation of nitroso acetals into amino acids derivatives, as well as TFA-catalyzed transformations of nitroso acetals, are examined to prove the possible utility of this umpolung procedure.

引用

页码：3377 / 3384

页数：8

共 2 条

[1] New C-C coupling reaction of cyclic nitronates with carbon nucleophiles. Umpolung of the conventional reactivity of nitronates
Smirnov, VO
Ioffe, SL
Tishkov, AA
Khomutova, YA
Nesterov, ID
Antipin, MY
Smit, WA
Tartakovsky, VA
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24): : 8485 - 8488
[2] Mild and efficient pentafluorophenylammonium triflate (PFPAT)-catalyzed C-acylations of enol silyl ethers or ketene silyl (thio)acetals with acid chlorides
Iida, Akira
Osada, Jun
Nagase, Ryohei
Misaki, Tomonori
Tanabe, Yoo
ORGANIC LETTERS, 2007, 9 (10) : 1859 - 1862

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