A Photochemical Synthesis of Functionalized trans-Cyclooctenes Driven by Metal Complexation

Maksim Royzen, Glenn P. A. Yap, and Joseph M. Fox*
Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716
J. Am. Chem. Soc., 2008, 130 (12), pp 3760–3761
DOI: 10.1021/ja8001919
Publication Date (Web): March 6, 2008
Copyright © 2008 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jmfox@udel.edu

Abstract

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Described is a scalable procedure for driving photochemical sytheses of trans-cyclooctene derivatives through metal complexation. During photoirradiation, reaction mixtures are continuously pumped through a column of a AgNO3-impregnated silica gel. The trans-cyclooctene derivative is selectively retained by the AgNO3-impregnated silica, but the cis-isomer elutes from the column back to the reaction flask, where it is photoisomerized and recirculated through the column. The method provides access to a range of usefully functionalized derivatives of trans-cyclooctene, including a derivative of 5-aza-trans-cyclooctene that underwent transannular cyclization upon treatment with bromine. The alkene stereochemistry is transferred with high fidelity to the hexahydropyrrolizine framework in the transannular cyclization.

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History

  • Published In Issue March 26, 2008
  • Received January 14, 2008

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