상세 보기
초록
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)].
키워드
beta-lactam; rhodium; palladium; C-H insertion; allylic alkylation; asymmetric catalysis; INSERTION REACTIONS; COOPERATIVE CATALYSIS; KINUGASA REACTION; AMINO ACIDS; DIAZOACETAMIDES; CONSTRUCTION; ANNULATION; KETENES; ECONOMY; PROGRESS
- 제목
- Asymmetric Rh(II)/Pd(0) Relay Catalysis: Synthesis of alpha-Quaternary Chiral beta-Lactams through Enantioselective C-H Insertion/Diastereoselective Allylation of Diazoamides
- 저자
- Huang, Liang-Zhu; Xuan, Zi; Jeon, Hyun Ji; Du, Zhen-Ting; Kim, Ju Hyun; Lee, Sang-gi
- 발행일
- 2018-08
- 유형
- Article
- 저널명
- ACS Catalysis
- 권
- 8
- 호
- 8
- 페이지
- 7340 ~ 7345