4.8 Article

Tetrahydroquinolines via Stereospecific [3+3]-Annulation of Donor-Acceptor Cyclopropanes with Nitrosoarenes

Journal

ORGANIC LETTERS
Volume 18, Issue 11, Pages 2784-2787

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01302

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Funding

  1. Deutsche Forschungsgemeinschaft (DFG)

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A stereospecific [3 + 3]-annulation of donor-acceptor cyclopropanes with nitrosoarenes under the influence of MgBr2 as a stoichiometric Lewis acid and reagent offers a novel approach to various structurally diverse C-8-brominated tetrahydroquinolines. In these cascades C-C, C-N, and C-Br bonds are formed. The reactions are easy to conduct and proceed under mild conditions, and the products can readily be further functionalized, rendering the method highly valuable.

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