Intermolecular exo-selective Diels-Alder reaction catalysed by dual-functional Bronsted acid: conformational restriction of transition states by hydrogen bonds as the key interaction.

ABSTRACT: An exo-selective Diels-Alder (exo-DA) reaction in which the formed diastereomer is different from that formed in the conventional endo-selective Diels-Alder (endo-DA) reaction was developed, which involves a dual-functional Brønsted acid as a catalyst and not only a dienophile (vinylquinoline) but also an acyclic diene (dienylcarbamate) having a sterically less demanding substituent. Factors necessary for achieving the exo-DA reaction were extracted through an exhaustive computational search of the corresponding transition states, in which the relative orientation of the dienophile and the acyclic diene is firmly defined by hydrogen bonding interactions with a dual-functional Brønsted acid catalyst. It was experimentally verified that the combined use of

SUBMITTER: Nakanishi T 

PROVIDER: S-EPMC10715229 | biostudies-literature | 2023 Dec

REPOSITORIES: biostudies-literature