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Alkylhalovinylboranes: a new class of Diels-Alder dienophiles.

ABSTRACT: The Diels-Alder reactions of alkylhalovinylboranes have been investigated theoretically and experimentally. Alkylhalovinylboranes presented higher reactivity than the corresponding dialkylvinylboranes. Although endo/exo selectivities were high for the reactions with cyclopentadiene, facial selectivities for the chiral analogues were low. Our results demonstrate that the replacement of an alkyl group on the boron atom by a halogen increases the dienophilicity considerably.

SUBMITTER: Pisano PL

PROVIDER: S-EPMC9086730 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Alkylhalovinylboranes: a new class of Diels-Alder dienophiles.

Pisano Pablo L PL Pellegrinet Silvina C SC

RSC advances 20180901 59

The Diels-Alder reactions of alkylhalovinylboranes have been investigated theoretically and experimentally. Alkylhalovinylboranes presented higher reactivity than the corresponding dialkylvinylboranes. Although <i>endo</i>/<i>exo</i> selectivities were high for the reactions with cyclopentadiene, facial selectivities for the chiral analogues were low. Our results demonstrate that the replacement of an alkyl group on the boron atom by a halogen increases the dienophilicity considerably. ...[more]

PMID: 35548792

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