CHED 298 |
| Beta-amino alcohols are an important functional group in natural products and pharmacological drugs. While beta-amino alcohols are traditionally synthesized using an expensive and toxic osmium catalyst, our group recently showed that copper (II) salts can catalyze the aminohydroxylation of alkenes with N-sulfonyl oxaziridines. In an interest to broaden the efficiency and utility of this reaction, the nature of the N-sulfonyl protecting group of the oxaziridine was modified. N-benzenesulfonyl oxaziridines that are substituted at the 4-position of the sulfonamide are of interest because they are easy to deprotect and have the potential to speed up the rate of the reaction. Herein we report the effect of varying the N-sulfonyl group of the oxaziridine on the aminohydroxylation reaction. We have systematically explored the effect of various electron-donating and –withdrawing substituents on the efficiency of this reaction. The benezenesulfonyl groups utilized include the para nitro, chloro, methoxy, methyl, and trifluoromethyl variants. |
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Undergraduate Research Poster Session
2:30 PM-4:30 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Chemical Education |