Journal
CHEMICAL COMMUNICATIONS
Volume 53, Issue 72, Pages 10030-10033Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7cc05595a
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Funding
- NSFC [21372002, 21232007]
- PAPD
- Natural Science Foundation of Jiangsu Province [BK20160003, BK20170227]
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A catalytic asymmetric decarboxylative [4+2] cycloaddition of vinyl benzoxazinanones with methyleneindolinones has been established, which provided a series of chiral tetrahydroquinoline-based 3,3'-spirooxindoles in high yields (up to 96%) and with excellent diastereo- and enantioselectivities (all >95 : 5 d.r., up to 99% ee). This reaction not only represents the first example of catalytic enantioselective [4+2] cycloaddition between methyleneindolinones and Pd-containing 1,4-dipoles, but also demonstrates the great practicability of catalytic asymmetric decarboxylative cycloadditions in the synthesis of enantio-enriched polycyclic compounds.
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