SHARPLESS EPOXIDATION
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The 'Sharpless epoxidation' reaction is an enantioselective chemical reaction to prepare 2,3-epoxyalcohols from primary and secondary allylic alcohols.[1][2] This reaction gives good yields and enantioselectivities over a broad range of substrates.
The oxidizing agent is t-butylperoxide. Enantioselectivity is achieved by a catalyst formed from titanium tetra(isopropoxide) and diethyl tartrate. Only 5-10 mol% of the catalyst in the presence of 3Ã… molecular sieves (3Ã… MS) is necessary.[3]
Several reviews have been published.[4][5][6][7]
Epoxides can be easily converted into dialcohols, aminoalcohols or ethers, so formation of chiral epoxides is a very important step in the synthesis of natural products. K. Barry Sharpless shared the Nobel prize in 2001 for his work on asymmetric oxidations.
The prize was shared with William S. Knowles and Ryoji Noyori.
The Sharpless group has investigated both the reaction kinetics[8] and the structure of the catalyst[9].
★ Asymmetric catalytic oxidation
1. Katsuki, T.; Sharpless, K. B. ''J. Am. Chem. Soc.'' '1980', ''102'', 5974. ()
2. Hill, J. G.; Sharpless, K. B.; Exon, C. M.; Regenye, R. ''Org. Syn.'', Coll. Vol. 7, p.461 (1990); Vol. 63, p.66 (1985). (Article)
3. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. ''J. Am. Chem. Soc.'' '1987', ''109'', 5765-5780. ()
4. Johnson, R. A.; Sharpless, K. B. ''Comp. Org. Syn.'' '1991', ''7'', 389-436. (Review)
5. Hüft, E. ''Top. Curr. Chem.'' '1993', ''164'', 63-77. (Review)
6. Katsuki, T.; Martin, V. S. ''Org. React.'' '1996', ''48'', 1-300. (Review)
7. Pfenninger, A. ''Synthesis'' '1986', 89-116. (Review)
8. Woodard, S. S.; Finn, M. G.; Sharpless, K. B. ''J. Am. Chem. Soc.'' '1991', ''113'', 106-113. ()
9. Finn, M. G.; Sharpless, K. B. ''J. Am. Chem. Soc.'' '1991', ''113'', 113-126. ()
★ Sharpless Asymmetric Epoxidation Reaction
The Sharpless epoxidation
The oxidizing agent is t-butylperoxide. Enantioselectivity is achieved by a catalyst formed from titanium tetra(isopropoxide) and diethyl tartrate. Only 5-10 mol% of the catalyst in the presence of 3Ã… molecular sieves (3Ã… MS) is necessary.[3]
Several reviews have been published.[4][5][6][7]
Epoxides can be easily converted into dialcohols, aminoalcohols or ethers, so formation of chiral epoxides is a very important step in the synthesis of natural products. K. Barry Sharpless shared the Nobel prize in 2001 for his work on asymmetric oxidations.
The prize was shared with William S. Knowles and Ryoji Noyori.
| Contents |
| Reaction mechanism |
| See also |
| References |
| External links |
Reaction mechanism
The Sharpless group has investigated both the reaction kinetics[8] and the structure of the catalyst[9].
See also
★ Asymmetric catalytic oxidation
References
1. Katsuki, T.; Sharpless, K. B. ''J. Am. Chem. Soc.'' '1980', ''102'', 5974. ()
2. Hill, J. G.; Sharpless, K. B.; Exon, C. M.; Regenye, R. ''Org. Syn.'', Coll. Vol. 7, p.461 (1990); Vol. 63, p.66 (1985). (Article)
3. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. ''J. Am. Chem. Soc.'' '1987', ''109'', 5765-5780. ()
4. Johnson, R. A.; Sharpless, K. B. ''Comp. Org. Syn.'' '1991', ''7'', 389-436. (Review)
5. Hüft, E. ''Top. Curr. Chem.'' '1993', ''164'', 63-77. (Review)
6. Katsuki, T.; Martin, V. S. ''Org. React.'' '1996', ''48'', 1-300. (Review)
7. Pfenninger, A. ''Synthesis'' '1986', 89-116. (Review)
8. Woodard, S. S.; Finn, M. G.; Sharpless, K. B. ''J. Am. Chem. Soc.'' '1991', ''113'', 106-113. ()
9. Finn, M. G.; Sharpless, K. B. ''J. Am. Chem. Soc.'' '1991', ''113'', 113-126. ()
External links
★ Sharpless Asymmetric Epoxidation Reaction
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