4.6 Article

Diastereoselective synthesis of spiro-cyclopropanyl-cyclohexadienones via direct sulfide-catalyzed [2+1] annulation of para-quinone methides with bromides

期刊

ORGANIC & BIOMOLECULAR CHEMISTRY
卷 18, 期 22, 页码 4257-4266

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob00778a

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资金

  1. National Natural Science Foundation of China [21961034, 21502154, 21362033]
  2. Science and Technology Program of Gansu Province [17JR5RA073, 18JR3RA091]

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An efficient sulfide-catalyzed [2 + 1] annulation ofpara-quinone methides (p-QMs) with diverse bromides has been achieved. This catalytic strategy provides an efficient and straightforward protocol for accessing a variety of spiro-cyclopropanyl-cyclohexadienone compounds in good to excellent yields (64% to 96% yields) with outstanding diastereoselectivities (>20 : 1 dr), displaying good functional group tolerance as well as gram-scale capacity.

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