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Copper‐Catalyzed [3+2] Cycloaddition and Interrupted Fischer Indolization to Prepare Polycyclic Furo[2,3‐b]indolines from N ‐Aryl Isatin Nitrones and Methylenecyclopropanes
Author(s) -
Wu SiYi,
Chen WeiLi,
Ma XiaoPan,
Liang Cui,
Su GuiFa,
Mo DongLiang
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801327
Subject(s) - chemistry , isatin , cycloaddition , aryl , cyclopropane , ring (chemistry) , catalysis , stereochemistry , medicinal chemistry , organic chemistry , alkyl
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.