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Issue 79, 2020

Selective ring-rearrangement or ring-closing metathesis of bicyclo[3.2.1]octenes

Author affiliations

Abstract

Explored was the competitive ring-closing metathesis vs. ring-rearrangement metathesis of bicyclo[3.2.1]octenes prepared by a simple and convergent synthesis from bicyclic alkylidenemalono-nitriles and allylic electrophiles. It was uncovered that ring-closing metathesis occurs exclusively on the tetraene-variant, yielding unique, stereochemically and functionally rich polycyclic bridged frameworks, whereas the reduced version (a triene) undergoes ring-rearrangement metathesis to 565 fused ring systems resembling the isoryanodane core.

Graphical abstract: Selective ring-rearrangement or ring-closing metathesis of bicyclo[3.2.1]octenes

Supplementary files

Article information


Submitted
07 Jul 2020
Accepted
11 Sep 2020
First published
11 Sep 2020

Chem. Commun., 2020,56, 11779-11782
Article type
Communication

Selective ring-rearrangement or ring-closing metathesis of bicyclo[3.2.1]octenes

E. Semenova, O. Lahtigui, S. K. Scott, M. Albritton, K. A. Abboud, I. Ghiviriga, A. E. Roitberg and A. J. Grenning, Chem. Commun., 2020, 56, 11779 DOI: 10.1039/D0CC04624H

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