Development and evaluation of a solid-supported cyclobutadieneiron tricarbonyl complex for parallel synthesis applications

ACS Combinatorial Science
Jason J Marineau, M L Snapper

Abstract

Cycloadditions of cyclobutadiene can offer rapid access to rigid polycyclic ring systems. Further functionalization of these strained-ring cycloadducts can lead to unique scaffolds for probing unexplored regions of chemical space. Along these lines, opportunities for high-throughput syntheses of these novel systems could be facilitated with the introduction of an immobilized cyclobutadiene reagent. Reported herein are preliminary studies of an iron tricarbonyl cyclobutadiene complex attached to solid support. Oxidative unmasking of the immobilized cyclobutadiene in the presence of various dienophiles is shown to produce a small collection of substituted bicyclo[2.2.0]hexene derivatives. The solid support cycloaddition strategy is shown to be comparable, but lower in efficiency to solution phase methods for generating these cycloadducts.

References

Jul 18, 2001·Journal of the American Chemical Society·H L DeakM L Snapper
Dec 6, 2002·Journal of the American Chemical Society·John LimantoMarc L Snapper
Dec 17, 2004·Nature·Christopher M Dobson
Dec 17, 2004·Nature·Brent R Stockwell
Dec 17, 2004·Nature·Christopher Lipinski, Andrew Hopkins
Jul 12, 2005·Angewandte Chemie·Benjamin A SeigalMarc L Snapper
Dec 16, 2005·Organic Letters·Holly L DeakMarc L Snapper
Nov 3, 2006·Organic Letters·Andrew J Leyhane, Marc L Snapper
Oct 22, 2008·Chemical Communications : Chem Comm·Emma E WyattDavid R Spring
Jun 18, 2009·Chemical Communications : Chem Comm·Warren R J D GallowayDavid R Spring

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