AI Article Synopsis
- Enzymatic dioxygenation of benzyl azide by toluene dioxygenase yields enantiopure cis-cyclohexadienediol and an exocyclic diene via two spontaneous [3,3] sigmatropic shifts.
- The resulting dienediol has significant potential for natural product synthesis due to its unique structure.
- The sigmatropic rearrangements can be reversed by protecting the diol, and an optimized production protocol for these diols is provided.
Article Abstract
Enzymatic dioxygenation of benzyl azide by toluene dioxygenase produces the expected enantiopure cis-cyclohexadienediol along with an exocyclic diene formed by a spontaneous sequence of two [3,3] sigmatropic shifts. This novel dienediol presents high synthetic potential for natural product synthesis. The sigmatropic rearrangements can be reversed by protection of the diol moiety. An optimized production protocol for either of these valuable diols is presented.
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| http://dx.doi.org/10.1021/ol503708v | DOI Listing |
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