Alkylhalovinylboranes: a new class of Diels-Alder dienophiles

Date

2018-10-02

Journal Title

Journal ISSN

Volume Title

Publisher

Royal Society of Chemistry
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.

Keywords

Alkylhalovinylboranes, Diels Alder reaction, Dienophiles, Organoboron compounds, Boron, Cyclopentanes, Halogens, Alkyl, Rational design

Citation

Pisano, P. L. and Pellegrinet, S. C. (2018). Alkylhalovinylboranes: a new class of Diels-Alder dienophiles. RSC Advances, 12(59), 33864-33871. https://doi.org/10.1039/C8RA07089J