Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 16, Issue 13, Pages 1730-1734Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202100372
Keywords
rhodium; hydrosilane; diastereoselectivity; cycloisomerization reaction; 1; 6-dienes
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Funding
- National Natural Science Foundation of China [21773051, 22072035, 21801056, 21901056]
- Zhejiang Provincial Natural Science Foundation of China [LZ18B020001, LQ19B040001]
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Organosilicon compounds are important reagents and intermediates in the construction of new materials and complex products. In this study, a highly diastereoselective rhodium-catalyzed cycloisomerization reaction was demonstrated using (EtO)3SiH to accelerate the cyclization reaction and yield spiro-fused succinimide and pyrazolone derivatives as a single diastereoisomer. The proposed mechanism involves an active Rh-H species from the hydrosilane as the H-donor in the spiro-type cycloisomerization reaction.
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)(3)SiH 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.
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