Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 32, Pages 10293-10298Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201803541
Keywords
alkynes; donor-acceptor cyclopropanes; gallium halides; trans addition; vinyl halides
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Funding
- Russian Science Foundation [14-13-01054-P]
- Program of Fundamental Research of State Academies of Sciences [01201363817]
- Russian Science Foundation [17-13-00080] Funding Source: Russian Science Foundation
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A new strategy for the three-component addition of halide anions and acetylenes to donor-acceptor cyclopropanes (DACs) is presented. This reaction, which occurs with high E selectivity, is promoted by gallium(III) salts and based on the 1,2-zwitterionic reactivity of DACs. It opens up a new group of processes involving DACs. The reaction occurs readily with a broad range of substrates and is tolerant of various functional groups. This methodology makes it possible to assemble highly functionalized vinyl halides, which are very convenient building blocks in organic synthesis. A possible mechanism of this reaction and its stereochemical aspects are discussed in detail.
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