A mild oxidation method of hydroxamic acids: efficient trapping of acyl nitroso intermediates

被引：58

作者：

Iwasa, S ^{[1
]}

Tajima, K ^{[1
]}

Tsushima, S ^{[1
]}

Nishiyama, H ^{[1
]}

机构：

[1] Toyohashi Univ Technol, Sch Mat Sci, Toyohashi, Aichi 4418580, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 34期

关键词：

nitroso intermediate; hydrogen peroxide; ruthenium catalyst; hetero Diels-Alder reaction; 1,2-oxazine;

D O I：

10.1016/S0040-4039(01)01119-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ruthenium(II)-pyridine-2,6-dicarboxylate (pydic) of 2,6-bis(oxazolinyl)pyridine (pybox-dh) complex catalyzed the hydrogen peroxide oxidation of hydroxamic acid in the presence of cyclopentadiene to give acyl nitroso cycloadducts in 74-99% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

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收藏

页码：5897 / 5899

页数：3

相关论文

共 32 条

[1] Steric and conformational control of the regioselectivities in the ene reaction with trisubstituted cycloalkenes: Comparison of the enophiles singlet oxygen, triazolinedione, and nitrosoarene [J].

Adam, W ;

Bottke, N ;

Krebs, O .

ORGANIC LETTERS, 2000, 2 (21) :3293-3296

[2]

ALBINI A, 1993, SYNTHESIS-STUTTGART, P263

[3] Total synthesis of (-)-epibatidine using an asymmetric Diels-Alder reaction with a chiral N-acylnitroso dienophile [J].

Aoyagi, S ;

Tanaka, R ;

Naruse, M ;

Kibayashi, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8397-8406

[4] First asymmetric hetero Diels-Alder reaction of 1-sulfinyl dienes with nitroso derivatives.: A new entry to the synthesis of optically pure 1,4-imino-1-ribitol derivatives [J].

Arribas, C ;

Carreño, MC ;

García-Ruano, JL ;

Rodríguez, JF ;

Santos, M ;

Sanz-Tejedor, MA .

ORGANIC LETTERS, 2000, 2 (20) :3165-3168

[5] SELECTIVE OXIDATION OF ALCOHOLS BY A H2O2-RUCL3 SYSTEM UNDER PHASE-TRANSFER CONDITIONS [J].

BARAK, G ;

DAKKA, J ;

SASSON, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3553-3555

[6] RUTHENIUM-CATALYZED OXIDATION OF PRIMARY ALCOHOLS WITH THE NEW OXIDATION SYSTEM N-METHYLMORPHOLINE/HYDROGEN-PEROXIDE [J].

BEHR, A ;

EUSTERWIEMANN, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 403 (1-2) :215-219

[7] DIELS-ALDER REACTIONS OF AZADIENES [J].

BOGER, DL .

TETRAHEDRON, 1983, 39 (18) :2869-2939

[8]

BOGER DL, 1987, HETERO DIELSALDER ME

[9]

Carruthers W, 1990, Cycloaddition Reactions in Organic Synthesis

[10] FORMATION AND INTERCONVERSION OF OXAZINES AND DIOXAZINES FROM THE REACTION OF NITROSOCARBONYL COMPOUNDS WITH CYCLOPENTADIENES [J].

DAO, LH ;

DUST, JM ;

MACKAY, D ;

WATSON, KN .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (13) :1712-1719

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