Rh( iii )-catalyzed sequential spiroannulation/lactonization of 3-aryl N -sulfonyl ketimines with 4-hydroxy-2-alkynoates by C–H bond activation

A sequential rhodium( iii )-catalyzed spiroannulation and lactonization strategy has been developed for the synthesis of a highly rigid spirobenzosultam lactones in good yields with high regioselectivity by means of aromatic ortho -C–H bond activation/functionalization of 3-aryl N -sulfonyl ketimine...

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Bibliographic Details
Published in:New journal of chemistry 2024-04, Vol.48 (17), p.7646-7650
Main Authors: Prashanth, S., Ajay, Chidrawar, Nagesh, Kommu, Sridhar, B., Reddy, B. V. Subba
Format: Article
Language:English
Subjects:
Aromatic compounds
Hydrogen bonds
Imines
Lactones
Regioselectivity
Rhodium
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Summary:A sequential rhodium( iii )-catalyzed spiroannulation and lactonization strategy has been developed for the synthesis of a highly rigid spirobenzosultam lactones in good yields with high regioselectivity by means of aromatic ortho -C–H bond activation/functionalization of 3-aryl N -sulfonyl ketimines with 4-hydroxy-2-alkynoates. The reaction proceeds through a cascade of C–H activation followed by spiroannulation and lactonization. In this approach, two C–C and C–O bonds are formed in a single step. This is the first report on the spiroannulation of cyclic N -sulfonyl ketimines with hydroxyalkynoates.
ISSN:1144-0546
1369-9261
DOI:10.1039/D3NJ04312F