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Substrate controlled, regioselective carbopalladation for the one-pot synthesis of C4-substituted tetrahydroisoquinoline analogues.

ABSTRACT: 6-Exo-trig cyclization reaction through regioselective carbopalladation was demonstrated with N-(2-halobenzyl)-N-allylamines to furnish the corresponding C4-substituted tetrahydroisoquinoline derivatives. The scope of the reaction was extended to the synthesis of C4-quaternary tetrahydroisoquinoline derivatives also. The nature of the substituent on the olefin moiety dictates the course of the carbopalladation sequence. Regioselective carbopalladation is substantiated by performing the reaction with unsymmetrical diallylated amine substrates.

SUBMITTER: Krishna Reddy SM

PROVIDER: S-EPMC9052373 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Substrate controlled, regioselective carbopalladation for the one-pot synthesis of C4-substituted tetrahydroisoquinoline analogues.

Krishna Reddy Singarajanahalli Mundarinti SM Suresh Pavithira P Thamotharan Subbiah S Nanubolu Jagadeesh Babu JB Suresh Surisetti S Selva Ganesan Subramaniapillai S

RSC advances 20200421 27

6-Exo-trig cyclization reaction through regioselective carbopalladation was demonstrated with N-(2-halobenzyl)-N-allylamines to furnish the corresponding C4-substituted tetrahydroisoquinoline derivatives. The scope of the reaction was extended to the synthesis of C4-quaternary tetrahydroisoquinoline derivatives also. The nature of the substituent on the olefin moiety dictates the course of the carbopalladation sequence. Regioselective carbopalladation is substantiated by per ...[more]

PMID: 35493635

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