ORGN 389 |
| In connection with a total synthesis project, we required access to enantioenriched Diels-Alder dimers of ortho-quinols. The most straightforward approach to these compounds, via enantioselective oxidation of ortho-alkylphenols, has not been described. With this in mind, we have designed and prepared a new class of oxidants—chiral ortho-oxazolinyl-iodoxybenzenes. It is noteworthy that iodoxybenzene derivatives with a neutral nitrogen ligand at the ortho-position have not been previously reported, although many analogous compounds containing an oxygen ligand (carbonyl, sulfonyl, etc.) are known. The new chiral reagents have been found to achieve the desired transformation with significant levels of enantioselectivity.
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Asymmetric Reactions and Syntheses
8:00 AM-12:00 PM, Tuesday, August 21, 2007 BCEC -- 253C, Oral
Division of Organic Chemistry |
