Stereoselective synthesis of bicyclo[4.2.1]nonane skeletons by ring-closing metathesis: a new versatile methodology for the efficient assembly of functionalized cyclooctanoids

Organic Letters
Antoine MichautJean Rodriguez

Abstract

[reaction: see text] A new versatile methodology, resulting in a formal three-carbon ring expansion of cyclopentanones, for the efficient assembly of functionalized cyclooctanoids is described. The approach is based on the chemo-, regio-, and stereoselective alpha,gamma-difunctionalization of beta-ketoesters followed by ring-closing metathesis to form functionalized bicyclo[4.2.1]nonanes, precursors of the corresponding cyclooctanes, by selective ring cleavage of the one-carbon-atom bridge.

Citations

Feb 14, 2009·Chemical Communications : Chem Comm·Makoto ShimizuIsao Mizota
Jul 27, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Motoo Tori, Reiko Mizutani
Sep 18, 2020·Chemical Communications : Chem Comm·Evgeniya SemenovaAlexander J Grenning
Oct 17, 2009·Chemical Reviews·Wenyi Zhao

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