Enantioselective 1,3-dipolar cycloaddition of nitrones catalyzed by optically active cationic cobalt(III) complexes

被引：85

作者：

Mita, T ^{[1
]}

Ohtsuki, N ^{[1
]}

Ikeno, T ^{[1
]}

Yamada, T ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 15期

关键词：

D O I：

10.1021/ol026079p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] The optically active beta-ketoiminato cationic cobalt(Ill) complexes were employed as efficient Lewis acid catalysts for the enantioselective 1,3-dipolar cycloaddition reaction of alpha,beta-unsaturated aldehydes with nitrones. Excellent endo selectivities and high enantioselectivities were achieved in the cycloaddition reaction of 1-cyclopentene-1-carbaldehyde and the nitrones derived from 2-halobenzaidehyde.

引用

页码：2457 / 2460

页数：4

共 42 条

[1] Lewis-acid promoted addition of 2-trimethylsilyloxyfuran to nitrones: Synthesis and absolute configuration of tetrahydro-2-benzyl-3-(1-benzyloxyethyl)-furo[2,3-d]isoaxazol-5(2H) ones [J].

Castellari, C ;

Lombardo, M ;

Pietropaolo, G ;

Trombini, C .

TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :1059-1068

[2] 1,3-dipolar cycle additions catalyzed by bis(oxazoline)-magnesium-based chiral complexes. The importance of a Mg(II) counterion [J].

Desimoni, G ;

Faita, G ;

Mortoni, A ;

Righetti, P .

TETRAHEDRON LETTERS, 1999, 40 (10) :2001-2004

[3] Optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkenes: Applications in organic synthesis [J].

Frederickson, M .

TETRAHEDRON, 1997, 53 (02) :403-425

[4] Synthesis of and asymmetric cycloaddition with chiral diiron acyl complexes [J].

Gilbertson, SR ;

Lopez, OD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3399-3400

[5] Metal-catalyzed asymmetric 1,3-dipolar cycloaddition reactions [J].

Gothelf, KV ;

Jorgensen, KA .

ACTA CHEMICA SCANDINAVICA, 1996, 50 (08) :652-660

[6] TRANSITION-METAL-CATALYZED ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS BETWEEN ALKENES AND NITRONES [J].

GOTHELF, KV ;

JORGENSEN, KA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5687-5691

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

Gothelf, KV ;

Jorgensen, KA .

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

[8] A highly diastereoselective and enantioselective Ti(OTos)(2)-TADDOLate-catalyzed 1,3-dipolar cycloaddition reaction of alkenes with nitrones [J].

Gothelf, KV ;

Thomsen, I ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (01) :59-64

[9] Palladium(II)-catalyzed asymmetric 1,3-dipolar cycloaddition of nitrones to 3-alkenoyl-1,3-oxazolidin-2 ones [J].

Hori, K ;

Kodama, H ;

Ohta, T ;

Furukawa, I .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) :5017-5023

[10] ON MECHANISM OF 1,3-DIPOLAR CYCLOADDITIONS . AREPLY [J].

HUISGEN, R .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (06) :2291-&

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