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A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition.

ABSTRACT: A straightforward access to novel spiro[benzofuran-2,3'-pyrrolidine]-2',5'-diones based on the Rh2(esp)2-catalyzed insertion of carbenes derived from diazo arylidene succinimides (DAS) into the O-H bond of phenols is described. The initial adducts underwent a thermally promoted Claisen rearrangement followed by DABCO-catalyzed intramolecular 5-exo-trig oxa-Michael addition.

SUBMITTER: Vepreva A 

PROVIDER: S-EPMC9749547 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature

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A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition.

Vepreva Anastasia A   Yanovich Alexander A   Dar'in Dmitry D   Kantin Grigory G   Bunev Alexander A   Krasavin Mikhail M  

Beilstein journal of organic chemistry 20221206

A straightforward access to novel spiro[benzofuran-2,3'-pyrrolidine]-2',5'-diones based on the Rh<sub>2</sub>(esp)<sub>2</sub>-catalyzed insertion of carbenes derived from diazo arylidene succinimides (DAS) into the O-H bond of phenols is described. The initial adducts underwent a thermally promoted Claisen rearrangement followed by DABCO-catalyzed intramolecular 5-<i>exo</i>-<i>trig</i> oxa-Michael addition. ...[more]

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