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Asymmetric Rh(II)/Pd(0) Relay Catalysis: Synthesis of alpha-Quaternary Chiral beta-Lactams through Enantioselective C-H Insertion/Diastereoselective Allylation of Diazoamides
- Asymmetric Rh(II)/Pd(0) Relay Catalysis: Synthesis of alpha-Quaternary Chiral beta-Lactams through Enantioselective C-H Insertion/Diastereoselective Allylation of Diazoamides
- Huang, Liang-Zhu; Xuan, Zi; Jeon, Hyun Ji; Du, Zhen-Ting; Kim, Ju Hyun; Lee, Sang-gi
- Ewha Authors
- SCOPUS Author ID
- Issue Date
- Journal Title
- ACS CATALYSIS
- ACS CATALYSIS vol. 8, no. 8, pp. 7340 - 7345
- beta-lactam; rhodium; palladium; C-H insertion; allylic alkylation; asymmetric catalysis
- AMER CHEMICAL SOC
- SCIE; SCOPUS
- Document Type
- A straightforward route toward construction of a-quaternary chiral beta-lactam moiety via Rh(II)/Pd(0)-catalyzed stereoselective relay catalytic reaction is reported. This asymmetric dual relay catalysis involves Rh(II)-catalyzed enantioselective intramoluecular C-H insertions of alpha-diazoamides, and sequential Pd(0)-catalyzed diastereoselective intermolecular allylic alkylation. Under mild reaction conditions, a broad range of a-quaternary allylated chiral beta-lactams have been synthesized in high yields (up to 99%) with excellent stereoselectivities [up to diastereomeric ratio (dr) >99:1, up to 98% enantiomeric excess (ee)].
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