Complex bearing non-heme N4 ligand for the asymmetric epoxidation of olefins

Journal of Molecular Catalysis

Volumn 28, Issue 3, 2014, Pages 204-209

  Wang, Xiao E ^a,b   Miao, Cheng Xia ^a   Wang, Shou Feng ^a   Sun, Wei ^a  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Asymmetric epoxidation reaction; Manganese; Non heme

Indexed keywords

EPOXIDATION; KETONES; MANGANESE; OLEFINS; PORPHYRINS; SYNTHESIS (CHEMICAL);

ASYMMETRIC EPOXIDATION; METAL PRECURSOR; NON-HEME; OPTIMIZED CONDITIONS; UNSATURATED KETONES;

LIGANDS;

EID: 84904729570     PISSN: 10013555     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

1. Gelalcha F G, Bitterlich B, Beller M, et al. Iron-catalyzed asymmetric epoxidation of aromatic alkenes using hydrogen peroxide [J]. Angew Chem Int Ed, 2007, 46: 7293-7296.
2. McGarrigle E M, Gilheany D G. Chromium- and manganese-salen promoted epoxidation of alkenes [J]. Chem Rev, 2005, 105: 1563-1602.
3. Wong O A, Shi Y. Organocatalytic oxidation. asymmetric epoxidation of olefins catalyzed by chiral ketones and iminium salts [J]. Chem Rev, 2008, 108: 3958-3987.
4. Faveri G D, Ilyashenko G, Watkinson M. Recent advances in catalytic asymmetric epoxidation using the environmentally benign oxidant hydrogen peroxide and its derivatives [J]. Chem Soc Rev, 2011, 40: 1722-1760.
5. Zhang W, Loebach J L, Jacobsen E N, et al. Enantioselective epoxidation of unfunctionalized olefins catalyzed by salen manganese complexes [J]. J Am Chem Soc, 1990, 112: 2801-2803.
6. Irie R, Noda K., Katsuki T, et al. Catalytic asymmetric epoxidation of unfunctionalized olefins [J]. Tetrahedron Lett, 1990, 31: 7345-7348.
7. Ding Hao, Gao Bao-jiao, Cheng Wei. J Mol Catal, 2013, 27(2): 115-123.
8. Tu Xiao-bo, Fu Xiang-kai, Hu Xiao-yan, et al. J Mol Catal, 2010, 24(1): 12-19.
9. Gelalcha F G, Bitterlich B, Beller M, et al. Iron-catalyzed asymmetric epoxidation of aromatic alkenes using hydrogen peroxide [J]. Angew Chem Int Ed, 2007, 46: 7293-7296.
10. 2 [J]. J Am Chem Soc, 2001, 123: 7194-7195.
11. Murphy A, Dubois G, Stack T D P. Efficient epoxidation of electron-deficient olefins with a cationic manganese complex [J]. J Am Chem Soc, 2003, 125: 5250-5251.
12. Gómez L, Garcia-Bosch I, Costas M, et al. Chiral manganese complexes with pinene appended tetradentate ligands as stereoselective epoxidation catalysts [J]. Dalton Trans, 2007, 5539-5545.
13. Guillemot G, Neuburger M, Pfaltz A. Synthesis and metal complexes of chiral C2-Symmetric diamino-biso- xazoline ligands [J]. Chem Eur J, 2007, 13: 8960-8970.
14. Wu M, Wang B, Sun W, et al. Asymmetric epoxidation of olefins with chiral bioinspired manganese complexes [J]. Org Lett, 2009, 11: 3622-3625.
15. Wu Mei, Wang Bin, Wang Shou-feng, Sun Wei. J Mol Catal, 2010, 24(3): 235-239.
16. 2 on Fe and Mn aminopyridine catalysts: Probing the nature of active species by combined electron paramagnetic resonance and enantioselectivity study [J]. ACS Catal, 2012, 2: 1196-1202.
17. Garcia-Bosch I, Gómez L, Polo A, et al. Stereoselective epoxidation of alkenes with hydrogen peroxide using a bipyrrolidine-based family of manganese complexes [J]. Adv Syn Catal, 2012, 354: 65-70.
18. 4 ligand for enantioselective epoxidation of olefins [J]. Chem Eur J, 2012, 18: 6750-6753.
19. 2 catalyzed by electron-rich aminopyridine manganese catalysts [J]. Org Lett, 2013, 15: 6158-6161.
20. 2, catalyzed by non-heme iron and manganese complexes [J]. Coord Chem Rev, 2012, 256: 1418-1434.
21. Wang X E, Miao C X, Sun W, et al. Bioinspired manganese and iron complexes with tetradentate N ligands for the asymmetric epoxidation of olefins [J]. Chem Cat Chem, 2013, 5: 2489-2494.
22. Li Y W, Liu X Y, Zhao G, et al. 4-Substituted-α, α-diaryl-prolinols improve the enantioselective catalytic epoxidation of α, β-enones [J]. J Org Chem, 2007, 72: 288-291.
23. Oloo W N, Meier K K, Wang Y, et al. Identification of a low-spin acylperoxoiron(III) intermediate in bio-inspired non-heme iron-catalysed oxidations [J]. Nature Commun, 2014, 5: 3046-3055.