Stereocontrolled Construction of 1-Vinylindanes via Intramolecular Cyclization of o-Cinnamyl Chalcones.
Nein-Chen HsuehKai-Shang LaiMeng-Yang ChangPublished in: The Journal of organic chemistry (2018)
In this paper, a concise route for the synthesis of 1-vinylindanes is described, including (i) NaBH4-mediated reduction of o-cinnamyl chalcones and (ii) sequential BF3·OEt2-mediated intramolecular annulation of the resulting alkenols. The plausible mechanism is proposed and discussed herein. This protocol provides highly effective stereocontrolled cinnamyl-enone cross-coupling to construct three contiguous trans- trans stereocenters and one ( E)-configured alkenyl or styryl group.