Regioselective synthesis of aniline-derived 1,3- and Ci-symmetric 1,4-diols from trans-1,4-cyclohexadiene dioxide.
نویسندگان
چکیده
trans-Diepoxide 1 is well-known to react with aliphatic amines and the azide ion to give exclusively the 1,3-diol products. However, we observed that by judicious choice of conditions, reaction with anilines can give predominantly the 1,3-diol (3) or the heretofore rarely seen C(i)-symmetric 1,4-diol (4). Synthesis of an unsymmetrical 1,4-diol from two different anilines is also demonstrated. These studies demonstrate that an intramolecular anilino-NH hydrogen bond donor can direct Fürst-Plattner epoxide opening.
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ورودعنوان ژورنال:
- Organic letters
دوره 12 3 شماره
صفحات -
تاریخ انتشار 2010