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Cyclopropenes in Metallacycle-Mediated Cross-Coupling with Alkynes: Convergent Synthesis of Highly Substituted Vinylcyclopropanes

Author:
O’Rourke, Natasha F., Micalizio, Glenn C.
Source:
Organic letters 2016 v.18 no.6 pp. 1250-1253
ISSN:
1523-7052
Subject:
alkynes, chemical structure, cross-coupling reactions, diastereoselectivity, regioselectivity
Abstract:
Stereodivergent metallacycle-mediated cross-coupling reactions are described for the synthesis of densely functionalized vinylcyclopropanes from the union of alkynes with cyclopropenes. Strategies explored include hydroxyl-directed and nondirected processes, with the latter of these delivering vinylcyclopropanes with exquisite levels of regio- and stereoselectivity. Challenges inherent to these coupling reactions include diastereoselectivity (with respect to the cyclopropene) and regioselectivity (with respect to both coupling partners).
Agid:
5792485