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Molecular design principles towards exo-exclusive Diels-Alder reactions.

ABSTRACT: The exo selective Diels-Alder reactions, reported as special cases, usually involve catalytic reaction conditions and specific cyclic structural motifs on the diene and/or the dienophile. Here we report a systematic computational investigation on the substituent effect for simple, linear dienes and dienophiles towards exo control in Diels-Alder reactions under thermal conditions. Through detailed characterization of reaction pathways for Diels-Alder cycloadditions between linear dienes and dienophiles with various substituents, we summarize a set of design principles aiming for an optimal and nearly-exclusive exo selectivity. These results shall lead to valuable guidelines and more versatile strategies in organic synthesis that are in accordance with the principles of green chemistry.

SUBMITTER: Huang CJ

PROVIDER: S-EPMC9061082 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Molecular design principles towards exo-exclusive Diels-Alder reactions.

Huang Ci-Jhang CJ Li Elise Y EY

RSC advances 20190304 13

The exo selective Diels-Alder reactions, reported as special cases, usually involve catalytic reaction conditions and specific cyclic structural motifs on the diene and/or the dienophile. Here we report a systematic computational investigation on the substituent effect for simple, linear dienes and dienophiles towards exo control in Diels-Alder reactions under thermal conditions. Through detailed characterization of reaction pathways for Diels-Alder cycloadditions between linear di ...[more]

PMID: 35519943

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