Highly diastereoselective epoxidation of α,β-unsaturated carbonyl compounds using sodium peroxide

Letters in Organic Chemistry

Volumn 2, Issue 2, 2005, Pages 128-131

  Reddy, Valluru Krishna ^a   Haritha, Buchammagari ^b   Yamashita, Mitsuji ^b  

^a KYOTO UNIVERSITY   (Japan)

^b SHIZUOKA UNIVERSITY   (Japan)

Author keywords

Carbonyl compounds; Epoxides; Reaction kinetics; Reaction mechanism; Sodium peroxide

Indexed keywords

EID: 33750532847     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178053202964     Document Type: Review

References (19)

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7. No difficulties have been encountered in the handling of sodium peroxide although we conducted large scale preparations of phospholane epoxides. However, normal precautions associated with the handling of peroxides should be followed.
8. For our first communication on sodium peroxide epoxidation of 2-phospholene oxides, see: Yamashita, M.; Krishna Reddy, V.; Rao, L. N.; Haritha, B.; Maeda, M.; Suzuki, K.; Totsuka, H.; Takahashi, M.; Oshikawa, T. Tetrahedron Lett. 2003, 44, 2339.
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11. 4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel using 4% EtOAc in n-hexane as the eluent, to give pure epoxides 2a-1 in ≤90% yields; (b) The similar experimental procedure is followed to prepare epoxides 3, 4 and 5.
12. (E)-Chalcones (1a-1) were prepared by alkaline aldol condensation of the appropriately para-substituted benzaldehydes and/or para-substituted acetophenones as previously described by Kohler, E. P.; Chadwell, H. M. In Organic Synthesis; Gilman, H.; Blatt, A., H. Eds.; Wiley and Sons, New York, 1941; Vol. 1, p 78.
13. All of the epoxidation products are well known compounds. For spectroscopic and physical data, see: (a) Ochiai, M.; Nakakishi, A.; Suefuji, T. Org. Lett. 2000, 2, 2923;
14. (b) Tanaka, Y.; Nishimura, K.; Tomioka, K. Tetrahedron 2003, 59, 4549;
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17. (a) For reaction kinetics, see: Wang, B.; Kang, Y.-R.; Yang, L.-M.; Suo, J.-S. J. Mol. Cat. A: Chemical 2003, 203, 29;
18. 2) was determined by iodometric titration analysis data, using 0.1N sodium thiosulfate standard solution, and followed by the procedure described in Vogel's Text Book of Quantitative Inorganic Analysis, 4th Edition, Longman, London, p 381.
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