A Facile Approach to Oximes and Ethers by a Tandem NO+‐Initiated Semipinacol Rearrangement and H‐Elimination |
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| Authors: | Jia‐Wei Dong Dr. Tongmei Ding Prof. Dr. Shu‐Yu Zhang Prof. Dr. Zhi‐Min Chen Prof. Dr. Yong‐Qiang Tu |
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| Affiliation: | 1. School of Chemistry and Chemical Engineering and, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, P. R. China;2. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, P. R. China |
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| Abstract: | An efficient oximation method has been developed on the basis of NO+‐initiated semipinacol rearrangement and subsequent proton elimination. The procedure enabled the rapid construction of a series of oximes and oxime ethers with spiro quaternary stereocenters from allylic silyl ethers. Additional features of this reaction include wide substrate tolerance as well as the commercial availability of the safe nitrosation reagent NOBF4. The key N‐heterotricyclic cores of three natural alkaloids, tuberostemoninol B, (+)‐quebrachidine, and an insecticide, were also constructed efficiently by this method. |
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| Keywords: | oximes oxime ethers quaternary centers semipinacol rearrangement spiro compounds |
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