Journal
ACS CATALYSIS
Volume 8, Issue 8, Pages 7340-7345Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b01687
Keywords
beta-lactam; rhodium; palladium; C-H insertion; allylic alkylation; asymmetric catalysis
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Funding
- Samsung Science and Technology Foundation [SSTF-BA1401-10]
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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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