Catalytic enantioselective oxidations using molecular oxygen

Current Opinion in Drug Discovery and Development

Volumn 5, Issue 6, 2002, Pages 860-869

  Sigman, Matthew S ^a   Jensen, David R ^a   Rajaram, Sridhar ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Aerobic; Alcohol oxidation; Baeyer Villiger oxidation; Dihydroxylation; Enantioselective; Epoxidation; Oxidation; Oxidative biaryl coupling; Sulfoxidation

Indexed keywords

2 NAPHTHOL; ALCOHOL; ALKENE; ATOMOXETINE; BRUCINE; CINNAMYL ALCOHOL; COPPER; FLUOROBENZENE; FLUOXETINE; MANGANESE; METAL COMPLEX; NICKEL; OXIDIZING AGENT; OXYGEN; PALLADIUM; PORPHYRIN DERIVATIVE; PSYCHOSTIMULANT AGENT; RUTHENIUM; SCHIFF BASE; SPARTEINE; SULFOXIDE; VANADIUM;

ALCOHOL OXIDATION; ATOM; BAEYER VILLIGER REACTION; CATALYSIS; CHEMICAL REACTION; DIHYDROXYLATION; ENANTIOSELECTIVITY; EPOXIDATION; OXIDATION; OXIDATIVE BIARYL COUPLING; REVIEW; SULFOXIDATION;

ANIMALS; CATALYSIS; HUMANS; OXIDATION-REDUCTION; OXYGEN; PHARMACEUTICAL PREPARATIONS; STEREOISOMERISM; TECHNOLOGY, PHARMACEUTICAL;

EID: 0036869538     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (35)

1. 4-porphyrinato)ruthenium(VI) complex. Chem Commun (1998) 15:1583-1584.
2. Yamada T, Imagawa K, Nagata T, Mukaiyama T: Aerobic enantioselective epoxidation of unfunctionalized olefins catalyzed by optically active salen-manganese(III) complexes. Bull Chem Soc Jpn (1994) 67:2248-2256.
3. Imagawa K, Nagata T, Yamada T, Mukaiyama T: N-alkyl imidazoles as effective axial ligands in aerobic asymmetric epoxidation of unfunctionalized olefins catalyzed by optically active managanese(III)-salen type complex. Chem Lett (1994):527-530.
4. Nagata T, Imagawa K, Yamada T, Mukaiyama T: Enanatioselective aerobic epoxidation of acyclic simple olefins catalyzed by optically active β-ketoiminato managanes(III) complex. Chem Lett (1994):1259-1262.
5. Kureshy RI, Khan NH, Abdi SH, lyer P, Bhatt AK: Aerobic, enantioselective epoxidation of non-functionalized olefins catalyzed by Ni(II) chiral Schiff base complexes. J Mol Catalysis A Chem (1998) 130:41-50.
6. Kureshy RI, Khan NH, Abdi SH, Bhatt AK, lyer P: Synthesis, physicochemical studies and aerobic enantioselective epoxidation of non functionalized olefins catalyzed by new Co(II) chiral salen complexes. J Mol Catalysis A Chem (1997) 121:25-31.
7. Abdi SH, Kureshy RI, Khan NH, Bhadbhade MM, Suresh E: Enantioselective epoxidation reaction of non-functionalized prochiral alkenes using optically resolved [brucine](R)-[Ru(PDTA-H)Cl] and [brucine](S)-[Ru(PDTA-H)Cl] complexes. J Mol Catalysis A Chem (1999) 150:185-194.
8. Kureshy RI, Khan NH, Abdi SH, lyer P: Chiral Ru(III) metal complex-catalyzed aerobic enantioselective epoxidation of styrene derivatives with co-oxidation of aldehyde. J Mol Catalysis A Chem (1997) 124:91-97.
9. Kureshy RI, Khan NH, Abdi SH, Iyer P, Patel ST: Chiral Mn(III) Schiff base complex catalyzed aerobic enantioselective epoxidation of prochiral non-functionalized olefins. Polyhedron (1999) 18:1773-1777.
10. Zhang X, Han B, Hua YN, Huang MY, Jiang YY: Asymmetric epoxidation of cinnamyl alcohol catalyzed by silicasupported casein complex. Polym Advan Technol (2002) 13:216-219.
11. Bolm C, Schlingloff G, Weickhardt K: Optically active lactones from a Baeyer-Villiger-type metal-catalyzed oxidation with molecular oxygen. Angew Chem Int Ed (1994) 33:1848-1849.
12. Bolm C, Schlingloff G: Metal-catalyzed enantiospecific aerobic oxidation of cyclobutanones. Chem Commun (1995):1247-1248.
13. Ilmarinen K, Kriis K, Paju A, Pehk T, Lopp M: Synthesis of new N-tetrasubstituted derivatives of R,R-tartaric acid and their use as chiral ligands in oxidation catalysts. Proc Estonian Acad Sci Chem (2001) 5D:147-155.
14. Shinohara T, Fujioka S, Kotsuki H: Asymmetric Baeyer-Villiger oxidation of cyclobutanones using diethylzinc/oxygen/chiral amino alcohols. Heterocycles (2001) 55:237-242.
15. Imagawa K, Nagata T, Yamada T, Mukaiyama T: Asymmetric oxidation of sulfides with molecular oxygen catalyzed by β-oxo aldiminato manganese(III) complexes. Chem Lett (1995):335-336.
16. Nagata T, Imagawa K, Yamada T, Mukaiyama T: Enantioselective aerobic oxidation of sulfides catalyzed by optically active β-oxo aldiminatomanganeses(III) complexes. Bull Chem Soc Jpn (1995) 68:3241-3246.
17. Kolb HC, VanNiewenhze MS, Sharpless KB: Catalytic asymmetric dihydroxylation. Chem Rev (1994) 94:2483-2547.
18. Cairns JF, Roberts HL: Osmium tetroxide-catalyzed oxidation of olefins. J Chem Soc C (1968):642.
19. 2 in an asymmetric dihydroxylation.
20. Wirth T: Oxygen and osmium - A new alliance for dihydroxylations? Angew Chem Int Ed (2000) 39:334-335. Highlights of aerobic enantioselective dihydroxylation.
21. Döbler C, Mehltretter G, Sunderrneier U, Beller M: Osmium-catalyzed dihydroxylation of olefins using dioxygen or air as the terminal oxidant. J Am Chem Soc (2000) 122:10289-10297. Full investigation of Os-catalized aerobic asymmetric dihydroxylation.
22. 2- on ion-exchangers: The scope and reactivity using various cooxidants. J Am Chem Soc (2002) 124:5341-5349. Use of supported Os in an aerobic asymmetric dihydroxylation.
23. Krief A, Castillo CC: Catalytic asymmetric dihydroxylation of α-methylstyrene by air. Tetrahedron Lett (1999) 40:4189-4192. Use of catalytic selenoxides in an aerobic asymmetric dihydroxylation.
24. Nakajima M, Miyoshi I, Kanayama K, Hahimoto S, Noji M, Koga K: Enantioselective synthesis of binaphthol derivatives by oxidative coupling of naphthol derivatives catalyzed by chiral diamine-copper complexes. J Org Chem (1999) 64:2264-2271.
25. Li X, Yang J, Kozlowski MC: Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes. Org Lett (2001) 3:1137-1140.
26. Irie R, Masutani K, Katsuki T: Asymmetric aerobic oxidation couplings of 2-naphthol derivatives catalyzed by photoactivated chiral (NO)Ru(II)-salen complex. Synlett (2000) 10:1433-1436.
27. Chu C, Hwang D, Wang S, Uang B: Chiral oxovanadium complex catalyzed enantioselective oxidative coupling of 2-naphthols. Chem Commun (2001) 11:980-981.
28. Hon S, Li C, Kou J, Barhate NB, Liu Y, Wang Y, Chen C: Catalytic asymmetric coupling of 2-naphthols by chiral tridentate oxovanadium(IV) complexes. Org Lett (2001) 3:869-872.
29. Luo Z, Liu Q, Gong L, Cui X, Mi A, Jiang Y: The rational design of novel chiral oxovanadium(IV) complexes for highly enantioselective oxidative coupling of 2-naphthols. Chem Commun (2002) 8:914-915. Improved catalysts for enantioselective aerobic oxidative biaryl couplings.
30. Barhate N, Chen C: Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates. Org Lett (2002) 4:2529-2532. Improved catalysts for enantioselective aerobic oxidative biaryl couplings.
31. Masutani K, Uchida T, Irie R, Katsuki T: Catalytic asymmetric and chemoselective aerobic oxidation: Kinetic resolution of sec-alcohols. Tetrahedron Lett (2000) 41:5119-5123. First example of aerobic oxidative kinetic resolution of secondary alcohols.
32. Jensen DR, Pugsley JS, Sigman MS: Palladium-catalyzed enantioselective oxidations of alcohols using molecular oxygen. J Am Chem Soc (2001) 123:7475-7476. Pd-catalyzed aerobic oxidative kinetic resolution of secondary alcohols.
33. Ferreira EM, Stoltz BM: The palladium-catalyzed oxidative kinetic resolution of secondary alcohols with molecular oxygen. J Am Chem Soc (2001) 123:7725-7726. Pd-catalyzed aerobic oxidative kinetic resolution of secondary alcohols.
34. Ali IS, Sudalai A: Pd-catalyzed kinetic resolution of benzylic alcohols: A practical synthesis of (R)-tomoxetine and (S)-fluoxetine hydrochlorides. Tetrahedron Lett (2002) 43:5435-5436. Synthetic applications of the Pd-catalyzed aerobic oxidative kinetic resolution of secondary alcohols.
35. Mueller JM, Jensen DR, Sigman MS: Dual role of (-)q-sparteine in the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols. J Am Chem Soc (2002) 124:8202-8203. Mechanistic investigation of Pd-catalyzed oxidative kinetic resolution of secondary alcohols.