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Stereocontrolled Construction of 1-Vinylindanes via Intramolecular Cyclization of o-Cinnamyl Chalcones

Author:
Hsueh, Nein-Chen, Lai, Kai-Shang, Chang, Meng-Yang
Source:
Journal of organic chemistry 2018 v.83 no.18 pp. 11415-11424
ISSN:
1520-6904
Subject:
chalcones, cross-coupling reactions, cyclization reactions, enols, moieties, protocols
Abstract:
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.
Agid:
6146214