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

ABSTRACT: 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.

SUBMITTER: Wallbaum J

PROVIDER: S-EPMC5223275 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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

Wallbaum Jan J Garve Lennart K B LK Jones Peter G PG Werz Daniel B DB

Organic letters 20161214 1

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. ...[more]

PMID: 27966993

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