Journal of the American Chemical Society 2009-09-16

Reductive and brominative termination of alkenol cyclization in aerobic cobalt-catalyzed reactions.

Dominik Schuch, Patrick Fries, Maike Dönges, Bárbara Menéndez Pérez, Jens Hartung

Index: J. Am. Chem. Soc. 131(36) , 12918-20, (2009)

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Abstract

Tetrahydrofur-2-ylmethyl radicals were stereoselectively generated from substituted pent-4-en-1-ols in aerobic cobalt(II)-catalyzed oxidations. Intermediates were trapped with cyclohexa-1,4-diene, gamma-terpinene, BrCCl(3), diethyl dibromomalonate, or electron-deficient olefins such as acrylonitrile or dimethyl fumarate to afford functionalized tetrahydrofurans in synthetically useful yields.