| Unexpected Grob-type fragmentation of vinylogous β-silyloxy-cyclobutanone into γ-lactone |
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| 引用本文： | Xiang Wu,Wei-Dong Z. Li. Unexpected Grob-type fragmentation of vinylogous β-silyloxy-cyclobutanone into γ-lactone[J]. 中国化学快报, 2017, 28(5): 968-970. DOI: 10.1016/j.cclet.2016.12.017 |
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| 作者姓名： | Xiang Wu Wei-Dong Z. Li |
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| 作者单位： | a School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China;b Innovative Drug Research Centre, Chongqing University, Chongqing 401331, China |
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| 基金项目： | We are grateful for financial support from National Natural Science Foundation of China (NSFC, Nos. 21302177, 21672049 and 21672030). |
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| 摘 要： | An unusual formal oxy transposition of vinylogous β-silyloxy-cyclobutanone 1(a 1,5-difunctionalized substrate) under mild acidic conditions(aqueous HF in CH_3CN at 0℃) to the decalinic y-lactone 2 was described.A plausible mechanistic pathway involving the Grob-type fragmentation and intramolecularγ-Iactonization was proposed.
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| 关 键 词： | Grob fragmentation Vinylogous &beta -silyloxy-cyclobutanone Decalinic &gamma -lactone Oxy transposition Intramolecular &gamma -lactonization |
Unexpected Grob-type fragmentation of vinylogous β-silyloxy-cyclobutanone into γ-lactone |
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| Xiang Wu,Wei-Dong Z. Li. Unexpected Grob-type fragmentation of vinylogous β-silyloxy-cyclobutanone into γ-lactone[J]. Chinese Chemical Letters, 2017, 28(5): 968-970. DOI: 10.1016/j.cclet.2016.12.017 |
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| Authors: | Xiang Wu Wei-Dong Z. Li |
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| Affiliation: | a School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China;b Innovative Drug Research Centre, Chongqing University, Chongqing 401331, China |
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| Abstract: | An unusual formal oxy transposition of vinylogous β-silyloxy-cyclobutanone 1 (a 1,5-difunctionalized substrate) under mild acidic conditions (aqueous HF in CH3CN at 0℃) to the decalinic γ-lactone 2 was described. A plausible mechanistic pathway involving the Grob-type fragmentation and intramolecular γ-lactonization was proposed. |
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| Keywords: | Grob fragmentation Vinylogous β-silyloxy-cyclobutanone Decalinic γ-lactone Oxy transposition Intramolecular γ-lactonization |
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