Copper‐Catalyzed [3+2] Cycloaddition and Interrupted Fischer Indolization to Prepare Polycyclic Furo[2,3‐b]indolines from N‐Aryl Isatin Nitrones and Methylenecyclopropanes

Various polycyclic furo[2,3‐b]indolines containing a cyclopropane ring have been prepared in moderate yields with high diastereoselectivity from N‐aryl isatin nitrones and methylenecyclopropanes using a copper‐catalyzed [3+2] cycloaddition and subsequent interrupted Fischer indolization strategy und...

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Veröffentlicht in:Advanced synthesis & catalysis 2019-03, Vol.361 (5), p.965-970
Hauptverfasser: Wu, Si‐Yi, Chen, Wei‐Li, Ma, Xiao‐Pan, Liang, Cui, Su, Gui‐Fa, Mo, Dong‐Liang
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Sprache:eng
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Zusammenfassung:Various polycyclic furo[2,3‐b]indolines containing a cyclopropane ring have been prepared in moderate yields with high diastereoselectivity from N‐aryl isatin nitrones and methylenecyclopropanes using a copper‐catalyzed [3+2] cycloaddition and subsequent interrupted Fischer indolization strategy under mild reaction conditions. The obtained furo[2,3‐b]indolines were easily converted to piperidinone‐fused furo[2,3‐b]indolines by selective [1,3]‐rearrangement through N−O bond cleavage. Finally, two chiral polycyclic furo[2,3‐b]indolines were obtained by chiral auxiliary control.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201801327