Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 8, Issue 8, Pages 1436-1440Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201900378
Keywords
diastereoselectivity; 3-fluorooxindoles; photocatalysis; tetrahydroisoquinolines; visible light
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Funding
- Natural Science Foundation of Shanghai [16ZR1413800]
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The 3-fluorooxindole and tetrahydroisoquinoline scaffolds are both important structures because of their associated biological and pharmaceutical activities. Herein, we report a highly diastereoselective synthesis of 3-fluorooxindoles fully substituted at the 3-position and containing a tetrahydroisoquinoline fragment, through the visible-light photoredox-catalyzed cross-dehydrogenative coupling of tetrahydroisoquinolines with 3-fluorooxindoles. The protocol featured a wide substrate scope: N-alkyl-, N-haloalkyl-, N-aryl-, N-allyl-, N-propargyl-, and NH 3-fluorooxinloles were all able to be used to form the desired coupling products in up to 92% yield and 99 : 1 anti/syn.
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