Asymmetric 1,3-dipolar cycloaddition of nitrile oxides generated in situ by direct oxidation of aldoximes

被引：41

作者：

Tsuji, M ^{[1
]}

Ukaji, Y ^{[1
]}

Inomata, K ^{[1
]}

机构：

[1] Kanazawa Univ, Dept Chem Sci, Grad Sch Nat Sci & Technol, Kanazawa, Ishikawa 9201192, Japan

来源：

CHEMISTRY LETTERS | 2002年 / 11期

关键词：

D O I：

10.1246/cl.2002.1112

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric 1,3-dipolar cycloaddition of nitrile oxides, generated in situ from aldoximes by direct oxidation with tertbutyl hypochlorite, to 2-propen-1-ol was achieved by utilizing diisopropyl (R, R)-tartrate as a chiral auxiliary to afford the corresponding (R)-2-isoxazolines with high enantioselectivity up to 96% ee.

引用

页码：1112 / 1113

页数：2

共 18 条

[1]

Gothelf KV, 2002, CYCLOADDITION REACTIONS IN ORGANIC SYNTHESIS, P211

[2] Asymmetric 1,3-dipolar cycloaddition reactions [J].

Gothelf, KV ;

Jorgensen, KA .

CHEMICAL REVIEWS, 1998, 98 (02) :863-909

[3] Catalytic enantioselective 1,3-dipolar cycloaddition reactions of nitrones [J].

Gothelf, KV ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2000, (16) :1449-1458

[4] Chiral bis(trialkylsiloxymethyloxazolinyl)pyridine ligands. Highly enantioselective 1,3-dipolar cycloaddition reactions [J].

Iwasa, S ;

Tsushima, S ;

Shimada, T ;

Nishiyama, H .

TETRAHEDRON, 2002, 58 (02) :227-232

[5] New strategies for organic catalysis: The first enantioselective organocatalytic 1,3-dipolar cycloaddition [J].

Jen, WS ;

Wiener, JJM ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (40) :9874-9875

[6]

Kanemasa S, 2002, CYCLOADDITION REACTIONS IN ORGANIC SYNTHESIS, P249

[7] Synthesis of hydroximoyl chlorides from aldoximes and benzyltrimethylammonium tetrachloroiodate (BTMA ICl4) [J].

Kanemasa, S ;

Matsuda, H ;

Kamimura, A ;

Kakinami, T .

TETRAHEDRON, 2000, 56 (08) :1057-1064

[8] A PARTICULARLY CONVENIENT PREPARATION OF BENZOHYDROXIMINOYL CHLORIDES (NITRILE OXIDE PRECURSORS) [J].

LIU, KC ;

SHELTON, BR ;

HOWE, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (19) :3916-3918

[9] Enantioselective 1,3-dipolar cycloaddition of nitrones catalyzed by optically active cationic cobalt(III) complexes [J].

Mita, T ;

Ohtsuki, N ;

Ikeno, T ;

Yamada, T .

ORGANIC LETTERS, 2002, 4 (15) :2457-2460

[10] A SIMPLE REGIOSELECTIVE SYNTHESIS OF HYDROXIMINOYL CHLORIDES [J].

PEAKE, CJ ;

STRICKLAND, JH .

SYNTHETIC COMMUNICATIONS, 1986, 16 (07) :763-765

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