Enantioselective epoxidation of alkenes catalyzed by 2-fluoro-N-carbethoxytropinone and related tropinone derivatives

被引：64

作者：

Armstrong, A ^{[1
]}

Ahmed, G

Dominguez-Fernandez, B

Hayter, BR

Wailes, JS

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 24期

关键词：

D O I：

10.1021/jo026322y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several alpha-substituted N-carbethoxytropinones have been evaluated as catalysts for asymmetric epoxidation of alkenes with Oxone, via a dioxirane intermediate. alpha-Fluoro-N-carbethoxytropinone (2) has been studied in detail and is an efficient catalyst which does not suffer from Baeyer-Villiger decomposition and can be used in relatively low loadings. This ketone was prepared in enantiomerically pure form using chiral base desymmetrization of N-carbethoxytropinone. Asymmetric epoxidation catalyzed by 2 affords epoxides with up to 83% ee. Among other derivatives tested, the alpha-acetoxy derivative 7 affords the highest enantioselectivities.

引用

页码：8610 / 8617

页数：8

共 62 条

[1] Synthesis of optically active C2-symmetric ketones for the asymmetric epoxidation of prochiral olefins by dioxiranes generated in situ with Caroate™ as a peroxide source
Adam, W
Zhao, CG
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (24) : 3995 - 3998
[2] Asymmetric epoxidation of olefins by chiral dioxiranes generated in situ from ketones of D-(-)-quinic acid
Adam, W
Saha-Möller, CR
Zhao, CG
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (14) : 2749 - 2755
[3] Synthetic applications of nonmetal catalysts for homogeneous oxidations
Adam, W
Saha-Möller, CR
Ganeshpure, PA
[J]. CHEMICAL REVIEWS, 2001, 101 (11) : 3499 - 3548
[4] Synthesis of optically active α-hydroxy ketones by enantioselective oxidation of silyl enol ethers with a fructose-derived dioxirane
Adam, W
Fell, RT
Saha-Möller, CR
Zhao, CG
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (03) : 397 - 401
[5] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE
ADAM, W
BIALAS, J
HADJIARAPOGLOU, L
[J]. CHEMISCHE BERICHTE, 1991, 124 (10) : 2377 - 2377
[6] Transition state stereoelectronics in alkene epoxidations by fluorinated dioxiranes
Armstrong, A
Washington, I
Houk, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) : 6297 - 6298
[7] Asymmetric epoxidation catalyzed by esters of α-hydroxy-8-oxabicyclo[3.2.1]octan-3-one
Armstrong, A
Moss, WO
Reeves, JR
[J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (20) : 2779 - 2781
[8] Intramolecular epoxidation in unsaturated ketones and oxaziridines
Armstrong, A
Draffan, AG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (21): : 2861 - 2873
[9] Total synthesis of (+)-zaragozic acid C
Armstrong, A
Barsanti, PA
Jones, LH
Ahmed, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) : 7020 - 7032
[10] Exocyclic iminium salts as catalysts for alkene epoxidation by Oxone®
Armstrong, A
Ahmed, G
Garnett, I
Goacolou, K
Wailes, JS
[J]. TETRAHEDRON, 1999, 55 (08) : 2341 - 2352

← 1 2 3 4 5 6 7 →