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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

Title
Asymmetric Rh(II)/Pd(0) Relay Catalysis: Synthesis of alpha-Quaternary Chiral beta-Lactams through Enantioselective C-H Insertion/Diastereoselective Allylation of Diazoamides
Authors
Huang, Liang-ZhuXuan, ZiJeon, Hyun JiDu, Zhen-TingKim, Ju HyunLee, Sang-gi
Ewha Authors
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SCOPUS Author ID
이상기scopus
Issue Date
2018
Journal Title
ACS CATALYSIS
ISSN
2155-5435JCR Link
Citation
ACS CATALYSIS vol. 8, no. 8, pp. 7340 - 7345
Keywords
beta-lactamrhodiumpalladiumC-H insertionallylic alkylationasymmetric catalysis
Publisher
AMER CHEMICAL SOC
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
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)].
DOI
10.1021/acscatal.8b01687
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자연과학대학 > 화학·나노과학전공 > Journal papers
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