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Domino ring-opening-ring-closing enyne metathesis vs enyne metathesis of norbornene derivatives with alkynyl side chains. Construction of condensed polycarbocycles.

ABSTRACT: The metathesis of norbornene derivatives with alkynyl side-chain with Grubbs' ruthenium alkylidine as catalyst has been investigated with the objective of constructing condensed polycyclic structures. This investigation demonstrated that the generally observed domino reaction course involving a ring-opening metathesis of the norbornene unit and a ring-closing enyne metathesis is influenced to a great extent by the nature of the functional group and the substrate structure and may follow a different reaction course than what is usually observed. In cases where ROM-RCEYM occurred, the resulting 1,3-diene reacts in situ with the dienophile to provide condensed tetracyclic systems.

SUBMITTER: Datta R

PROVIDER: S-EPMC6204787 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Domino ring-opening-ring-closing enyne metathesis vs enyne metathesis of norbornene derivatives with alkynyl side chains. Construction of condensed polycarbocycles.

Datta Ritabrata R Ghosh Subrata S

Beilstein journal of organic chemistry 20181025

The metathesis of norbornene derivatives with alkynyl side-chain with Grubbs' ruthenium alkylidine as catalyst has been investigated with the objective of constructing condensed polycyclic structures. This investigation demonstrated that the generally observed domino reaction course involving a ring-opening metathesis of the norbornene unit and a ring-closing enyne metathesis is influenced to a great extent by the nature of the functional group and the substrate structure and may follow a differ ...[more]

PMID: 30410632

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