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Highly Diastereoselective Hydrosilane-Assisted Rhodium-Catalyzed Spiro-Type Cycloisomerization of Succinimide and Pyrazolone-Based Functional 1,6-Dienes |
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| Authors: | Hui-Lin Li Wei-Sheng Huang Fang-Ying Ling Dr Li Li Jun-Hao Yan Hao Xu Prof Dr Li-Wen Xu |
| Institution: | 1. Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education and Laboratory of Organosilicon Material Technology of Zhejiang Province College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 311121 P. R. China
The authors contributed equally.;2. Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education and Laboratory of Organosilicon Material Technology of Zhejiang Province College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 311121 P. R. China |
| Abstract: | Organosilicon compounds are important reagents and synthetic intermediates that play a key role in the construction of new materials and complex products. Here we show a highly diastereoselective rhodium-catalyzed cycloisomerization of 1,6-dienes, in which the use of (EtO)3SiH accelerates the intramolecular cyclization reaction to afford a novel spiro-fused succinimide and pyrazolone derivatives in moderate to excellent yields as a single diastereoisomer. The proposed mechanism involves an active Rh−H species from the hydrosilane that is the H-donor in this spiro-type cycloisomerization reaction. |
| Keywords: | rhodium hydrosilane diastereoselectivity cycloisomerization reaction 1 6-dienes |