Asymmetric Rh(II)/Pd(0) Relay Catalysis: Synthesis of alpha-Quaternary Chiral beta-Lactams through Enantioselective C-H Insertion/Diastereoselective Allylation of Diazoamides

作者：Huang, Liang-Zhu; Xuan, Zi; Jeon, Hyun Ji; Du, Zhen-Ting^*; Kim, Ju Hyun^*; Lee, Sang-gi^*

来源：ACS Catalysis, 2018, 8(8): 7340-7345.

DOI：10.1021/acscatal.8b01687

• beta-lactam
• rhodium
• palladium
• C-H insertion
• allylic alkylation
• asymmetric catalysis

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)].

• 出版日期2018-8
• 单位西北农林科技大学