Iron and ruthenium Lewis acid catalyzed asymmetric 1,3-dipolar cycloaddition reactions between nitrones and enals

被引：135

作者：

Viton, F

Bernardinelli, G

Kündig, EP

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

[2] Univ Geneva, Lab Xray Crystallog, CH-1211 Geneva, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 18期

关键词：

D O I：

10.1021/ja017814f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The single coordination-site transition metal Lewis acids [CpM(BIPHOP-F)][SbF6] (M = Fe, Ru) catalyze the [3+2] dipolar cycloaddition reaction between reactive nitrones and α,β-unsaturated aldehydes to give chiral isoxazolidines with ee values of 75 to >96%. The stereochemistry of the major enantiomer is consistent with an endo approach of the nitrone to the Cα-Si-face of the enal in the s-trans conformation in the (R,R)-catalyst site. The absolute configuration is based on an X-ray structure determination. Copyright © 2002 American Chemical Society.

引用

收藏

页码：4968 / 4969

页数：2

相关论文

共 23 条

[1]

ALI SA, 1988, TETRAHEDRON, V44, P5911

[2] A new chiral ligand for the Fe-Lewis acid catalysed asymmetric Diels-Alder reaction [J].

Bruin, ME ;

Kundig, EP .

CHEMICAL COMMUNICATIONS, 1998, (23) :2635-2636

[3] 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

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

Frederickson, M .

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

[5] 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

[6] Control of diastereo- and enantioselectivity in metal-catalyzed 1,3-dipolar cycloaddition reactions of nitrones with alkenes. Experimental and theoretical investigations [J].

Gothelf, KV ;

Hazell, RG ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) :346-355

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

Gothelf, KV ;

Jorgensen, KA .

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

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

Gothelf, KV ;

Jorgensen, KA .

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

[9] Palladium-catalyzed asymmetric 1,3-dipolar cycloaddition of nitrones to olefins [J].

Hori, K ;

Kodama, H ;

Ohta, T ;

Furukawa, I .

TETRAHEDRON LETTERS, 1996, 37 (33) :5947-5950

[10] 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