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