Journal
ORGANIC LETTERS
Volume 21, Issue 18, Pages 7298-7302Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02560
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Funding
- National Natural Science Foundation of China [21702139]
- 1000-Youth Talents Program [YJ201702]
- Fundamental Research Funds for the Central Universities
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A highly diastereo- and enantioselective [4 + 1] cycloaddition of para-quinone methides to alpha-halogenated ketones was realized by bifunctional phosphonium salt catalysis, furnishing functionalized 2,3-dihydrobenzofurans in high yields and excellent stereoselectivities (>20:1 dr and up to >99.9% ee). Mechanistic observations suggested that the reaction underwent a cascade intermolecular substitution/intramolecular 1,6-addition process. DFT calculations revealed the presence of multiple H-bonding interactions between the catalyst and the enolate intermediate in the stereodetermining transition states.
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