CHED 482 |
Benzohydroximoyl halides have been used in synthetic schemes to produce oxime ethers of predictable E or Z stereochemistry. We now report the synthesis of benzohydroximoyl halides of specific E or Z configuration containing a chiral N-alkoxy group. These compounds are produced by synthesizing a chiral N-alkoxyphthalimide via a Mitsunobu reaction. N-alkoxylamine is released from the phthalimide and reacted with benzoyl chloride to produce a chiral benzohydroxamate. This hydroxamate can then be converted to a chiral hydroximoyl halide. The stereochemistry of the resulting benzohydroximoyl halide will be discussed along with potential reaction schemes to convert it to a chiral oxime ether. |
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster
Division of Chemical Education |