DOI: 10.1021/ol0161965. Catalytic Asymmetric Dihydroxylation Using Phenoxyethoxymethyl-polystyrene (PEM)-Based Novel Microencapsulated Osmium Tetroxide (PEM-MC OsO<sub>4</sub>)

Catalytic Asymmetric Dihydroxylation Using Phenoxyethoxymethyl-polystyrene (PEM)-Based Novel Microencapsulated Osmium Tetroxide (PEM-MC OsO4)

10.1021/ol0161965

Crossref journal-article

American Chemical Society (ACS)

Organic Letters (316)

Bibliography

Kobayashi, S., Ishida, T., & Akiyama, R. (2001). Catalytic Asymmetric Dihydroxylation Using Phenoxyethoxymethyl-polystyrene (PEM)-Based Novel Microencapsulated Osmium Tetroxide (PEM-MC OsO4). Organic Letters, 3(17), 2649â2652.

Authors 3

Shū Kobayashi (first)
Tasuku Ishida (additional)
Ryo Akiyama (additional)

References 13 Referenced 103

{'key': 'ol0161965b00001/ol0161965b00001_1', 'first-page': '213', 'volume': '80', 'author': 'Review', 'year': '1980', 'journal-title': 'Chem. Rev.'} / Chem. Rev. by Review (1980)
{'key': 'ol0161965b00002/ol0161965b00002_1', 'first-page': '2547', 'volume': '94', 'author': 'Review', 'year': '1994', 'journal-title': 'Chem. Rev.'} / Chem. Rev. by Review (1994)
10.1021/jo00036a003 / J. Org. Chem. by Sharpless K. B. (1992)
10.1021/ja00287a050 / J. Am. Chem. Soc. by Ovalicin (1985)
{'key': 'ol0161965b00005/ol0161965b00005_1', 'first-page': '1190', 'volume': '1181', 'author': 'Review', 'year': '1999', 'journal-title': 'Synlett'} / Synlett by Review (1999)
10.1002/1521-3773(20010202)40:3<589::AID-ANIE589>3.0.CO;2-9 / Angew. Chem., Int. Ed. by Recently (2001)
10.1021/jo981127y / J. Org. Chem. by Nagayama S. (1998)
{'key': 'ol0161965b00007/ol0161965b00007_2', 'first-page': '11230', 'volume': '121', 'author': 'Kobayashi S.', 'year': '1999', 'journal-title': 'J. Am. Chem. Soc.'} / J. Am. Chem. Soc. by Kobayashi S. (1999)
{'key': 'ol0161965b00008/ol0161965b00008_1', 'first-page': '2986', 'volume': '120', 'author': 'Kobayashi S.', 'year': '1998', 'journal-title': 'J. Am. Chem. Soc.'} / J. Am. Chem. Soc. by Kobayashi S. (1998)
The usefulness of the SR-MAS NMR technique for structure determination of resins directly without cleavage from polymer supports has been demonstrated through the development of several useful reactions using cross-linked polystyrene-based resins in the solid-phase in our laboratories. (a) Kobayashi, S.; Akiyama, R.; Furuta, T.; Moriwaki, M.Mol. Online1998,2, 35−39. (b) Kobayashi, S.; Aoki, Y.Tetrahedron Lett.1998,39, 7345−7348. (c) Kobayashi, S.; Akiyama, R.Tetrahedron Lett.1998,39, 9211−9214. (d) Kobayashi, S.; Furuta, T.; Sugita, K.; Okitsu, O.; Oyamada, H.TetrahedronLett.1999,40, 1341−1344. (e) Aoki, Y.; Kobayashi, S.J. Comb. Chem.1999,1, 371−372. (f) Okitsu, O.; Oyamada, H.; Furuta, T.; Kobayashi, S.Heterocycles2000,52, 1143−1162. (g) Kobayashi, S.; Akiyama, R.; Kitagawa, H.J. Comb. Chem.2000,2, 438−440.
{'volume-title': 'M. Microcapsules and Nanoparticles in Medicine and Pharmacy', 'year': '1992', 'author': 'Compound C', 'key': 'ol0161965b00010/ol0161965b00010_1'} / M. Microcapsules and Nanoparticles in Medicine and Pharmacy by Compound C (1992)
Confirmed by fluorescence X-ray analysis.
Typical Experimental Procedure for the Catalytic AsymmetricDihydroxylation of Olefins.PEM-MC OsO4(43.7 mg, 5 mol %), (DHQD)2PHAL (21.5 mg, 5 mol %), K3Fe(CN)6(362.2 mg, 1.1 mmol), and K2CO3(152.0 mg, 1.1 mmol) were combined in H2O/acetone (1:1, 3.5 mL), and the heterogeneous slurry was stirred vigorously at 30 °C for 1 h. To this mixture was then added an olefin (0.55 mmol). After the mixture stirred for 2 h, K3Fe(CN)6(362.2 mg, 1.1 mmol) and K2CO3(152.0 mg, 1.1 mmol) were added again, and the mixture was further stirred for 2 h. Methanol (10 mL) was then added, and the mixture was stirred for 10 min. PEM-MC OsO4was separated by filtration and reused (reuse data are shown in Table 2, entry 7). The crude product was purified by chromatography on silica gel to afford the desiredcis-diol. The optical purity of the product was determined by HPLC analysis.

Dates

Type	When
Created	23 years, 1 month ago (July 26, 2002, 12:41 a.m.)
Deposited	2 years, 5 months ago (March 13, 2023, 6:48 p.m.)
Indexed	2 months, 2 weeks ago (June 11, 2025, 10:43 p.m.)
Issued	24 years, 1 month ago (July 21, 2001)
Published	24 years, 1 month ago (July 21, 2001)
Published Online	24 years, 1 month ago (July 21, 2001)
Published Print	24 years ago (Aug. 1, 2001)

Funders 0

None

BibTeX

@article{Kobayashi_2001, title={Catalytic Asymmetric Dihydroxylation Using Phenoxyethoxymethyl-polystyrene (PEM)-Based Novel Microencapsulated Osmium Tetroxide (PEM-MC OsO4)}, volume={3}, ISSN={1523-7052}, url={http://dx.doi.org/10.1021/ol0161965}, DOI={10.1021/ol0161965}, number={17}, journal={Organic Letters}, publisher={American Chemical Society (ACS)}, author={Kobayashi, Shū and Ishida, Tasuku and Akiyama, Ryo}, year={2001}, month=jul, pages={2649–2652} }

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