Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 6, Pages 1243-1248Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo01505a
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Funding
- Special Funds of the Taishan Scholar Program of Shandong Province [tsqn201812047]
- Natural Science Foundation of Shandong Province [ZR2017JL011]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
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Chiral phosphoric acid catalyzed a regio-, diastereo- and enantioselective reaction of isoxazol-5(4H)-ones with beta,gamma-alkynyl-alpha-imino esters, allowing for high yields of diverse alpha-imino allenoates with an adjacent quaternary carbon stereocenter and an axially chiral tetrasubstituted allene motif.
The chiral phosphoric acid catalyzed regio-, diastereo- and enantioselective reaction of isoxazol-5(4H)-ones with beta,gamma-alkynyl-alpha-imino esters has been developed. With the established methodology, gamma-addition of beta,gamma-alkynyl-alpha-imino esters and C-allenylation of isoxazol-5(4H)-ones were achieved with high regio- and stereoselectivities, affording diverse alpha-imino allenoates featuring an adjacent quaternary carbon stereocenter and an axially chiral tetrasubstituted allene motif in high yields.
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