Asymmetric Rh(II)/Pd(0) Relay Catalysis: Synthesis of alpha-Quaternary Chiral beta-Lactams through Enantioselective C-H Insertion/Diastereoselective Allylation of Diazoamides
- 주제(키워드) beta-lactam , rhodium , palladium , C-H insertion , allylic alkylation , asymmetric catalysis
- 주제(기타) Chemistry, Physical
- 설명문(일반) [Huang, Liang-Zhu; Du, Zhen-Ting] Northwest A&F Univ, Sch Pharm & Chem, Shaanxi Key Lab Nat Prod & Chem Biol, Yangling 712100, Shaanxi, Peoples R China; [Kim, Ju Hyun] Gyeongsang Natl Univ, Res Inst Nat Sci, Dept Chem Plus BK21, Jinju 52828, South Korea; [Huang, Liang-Zhu; Xuan, Zi; Jeon, Hyun Ji; Lee, Sang-gi] Ewha Womans Univ, Dept Chem & Nano Sci Plus BK21, Seoul 120750, South Korea
- 등재 SCIE, SCOPUS
- 발행기관 AMER CHEMICAL SOC
- 발행년도 2018
- URI http://www.dcollection.net/handler/ewha/000000156210
- 본문언어 영어
- Published As http://dx.doi.org/10.1021/acscatal.8b01687
초록/요약
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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