Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates.

Org Lett

Institut für Organische Chemie and ‡Institut für Anorganische and Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.

Published: January 2017

Donor-acceptor cyclopropanes with two geminal carboxylic esters are reacted with chalcogenyl chlorides and bromides to afford ring-opened products bearing the halogen atoms in the 1-position, adjacent to the donor, and the chalcogenyl residue in the 3-position next to the two acceptor groups. A variety of different donors (e.g., aryl, N, and O) are used. The stereospecificity of the reaction is demonstrated by using a chiral starting material.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5223275PMC
http://dx.doi.org/10.1021/acs.orglett.6b03375DOI Listing

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