Highly Diastereoselective Hydrosilane‐Assisted Rhodium‐Catalyzed Spiro‐Type Cycloisomerization of Succinimide and Pyrazolone‐Based Functional 1, 6‐Dienes. Issue 13 (18th May 2021)

• Record Type: Journal Article
• Authors: Li, Hui‐Lin; Huang, Wei‐Sheng; Ling, Fang‐Ying; Li, Li; Yan, Jun‐Hao; Xu, Hao; Xu, Li‐Wen
• Is Part Of: Chemistry, an Asian journal. Volume 16:Issue 13(2021)
• Page Start: 1730
• Page End: 1734
• Publication Date: 2021-05-18
• Subjects: rhodium -- hydrosilane -- diastereoselectivity -- cycloisomerization reaction -- 1, 6-dienes; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.202100372
• Languages: English
• ISSNs: 1861-4728

Abstract

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)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. Abstract : A highly diastereoselective rhodium‐catalyzed cycloisomerization of 1, 6‐dienes that is promoted by hydrosilane has been established to afford spiro‐fused succinimide and pyrazolone derivatives in moderate to excellent yields as a single diastereoisomer.