期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 17, 页码 12326-12335出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01215
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资金
- Ministry of Science and Technology of the Republic of China [MOST 107-2628-M-003-001-MY3]
An enantioselective synthesis of spiropyrazolone-fused cyclopenta[c]chromen-4-ones is demonstrated via a (3+2) cycloaddition reaction using cinchona-alkaloid derived hydrogen-bonding catalyst. The method provides high yields of adducts with five contiguous stereocenters, including a spiro all-carbon quaternary stereocenter with good to excellent stereoselectivities. The one-pot methodology can also be scaled up effectively.
An enantioselective synthesis of spiropyrazolone-fused cyclopenta[c]chromen-4-ones is demonstrated via a (3+2) cycloaddition reaction. The reactions of 3-homoacylcoumarins and alpha,beta-unsaturated pyrazolones in the presence of the cinchona-alkaloid derived hydrogen-bonding catalyst provide aforementioned spiropyrazolone-chromenone adducts bearing five contiguous stereocenters, of which one is the spiro all-carbon quaternary stereocenter in high yields (up to 98%) with good to excellent stereoselectivities (>25:1 dr and up to 99% ee). This one-pot methodology could also be practically demonstrated on a gram-scale with similar efficacy.
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