Tandem cross enyne metathesis (CEYM)-intramolecular Diels-Alder reaction (IMDAR). An easy entry to linear bicyclic scaffolds

A new tandem cross enyne metathesis (CEYM)-intramolecular Diels-Alder reaction (IMDAR) has been carried out. It involves conjugated ketones, esters or amides bearing a remote olefin and aromatic alkynes as the starting materials. The overall process enables the preparation of a small family of linea...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2015-08, Vol.11 (1), p.1486-1493
Main Authors: Miró, Javier, Sánchez-Roselló, María, Sanz, Álvaro, Rabasa, Fernando, Del Pozo, Carlos, Fustero, Santos
Format: Article
Language:English
Subjects:
bicyclic frameworks
Chemistry
cross enyne metathesis
Diels–Alder reaction
Full Research Paper
tandem reaction
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Summary:A new tandem cross enyne metathesis (CEYM)-intramolecular Diels-Alder reaction (IMDAR) has been carried out. It involves conjugated ketones, esters or amides bearing a remote olefin and aromatic alkynes as the starting materials. The overall process enables the preparation of a small family of linear bicyclic scaffolds in a very simple manner with moderate to good levels of diastereoselectivity. This methodology constitutes one of the few examples that employ olefins differently than ethylene in tandem CEYM-IMDAR protocols.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.11.161