4.7 Article

Enantioselective Construction of Spirooxindole-Fused Cyclopenta[c]chromen-4-ones Bearing Five Contiguous Stereocenters via a Stepwise (3+2) Cycloaddition

期刊

ADVANCED SYNTHESIS & CATALYSIS
卷 362, 期 8, 页码 1679-1685

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901655

关键词

spiro compounds; cyclopenta[c]chromen-4-ones; stepwise (3+2) cycloaddition; organic catalysis; 3-homoacylcoumarins

资金

  1. Ministry of Science and Technology of the Republic of China [MOST 107-2628-M-003-001-MY3]

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The bifunctional quinine-catalyzed stepwise (3+2) cycloaddition for the enantioselective construction of spirooxindole-fused cyclopenta[c]chromen-4-ones is developed. The reactions of 3-homoacylcoumarins and alkylidene oxindole electrophiles generate aforementioned spirooxindole-chromenone adducts bearing five contiguous stereocenters, of which one is the spiro all-carbon quaternary stereocenter in high yields (up to 99%) with excellent stereoselectivities (up to >20:1 dr and 99% ee). This methodology was investigated for three different alkylidene oxindole electrophiles and could also be practically demonstrated on a gram scale. Mechanistic investigations revealed that the (3+2) cycloaddition for the enantioselective synthesis of spirooxindole-fused cyclopenta[c]chromen-4-ones is proceeding via a stepwise reaction pathway.

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