Experimental study demonstrates copper-catalyzed oxa-Diels–Alder synthesis of isochromans from sultines, highlighting broad functional-group tolerance for complex heterocycles.
The development of an oxa-Diels–Alder reaction between sultines and carbonyl compounds is reported. o-Quinodimethanes, generated from sultines, undergo a [4+2]-cycloaddition with activated aldehydes or ketones in the presence of Cu(OTf)2 to provide a variety of functionalized isochromans, including spiroisochromans, in up to 99% yield. The developed protocol demonstrates broad functional-group compatibility and tolerates unprotected isatins bearing free NH-functionalities.
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Ngamnithiporn et al. (2024) studied this question.
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