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- Title
Through-Bond/Through-Space Anion Relay Chemistry Exploiting Vinylepoxides as Bifunctional Linchpins.
- Authors
Chen, Ming Z.; Gutierrez, Osvaldo; Smith, Amos B.
- Abstract
The development of new bifunctional linchpins that permit the union of diverse building blocks is essential for the synthetic utility of anion relay chemistry (ARC). The design, synthesis, and validation of three vinylepoxide linchpins for through-bond/through-space ARC are now reported. For negative charge migration, this class of bifunctional linchpins employs initial through-bond ARC by an SN2′ reaction, followed by through-space ARC exploiting a 1,4-Brook rearrangement. The trans-disubstituted vinylepoxide linchpin yields a mixture of E/ Z isomers, whereas the cis-disubstituted and the trans-trisubstituted vinylepoxide linchpins proceed to deliver three-component adducts with excellent E selectivity.
- Subjects
ANIONS; EPOXY compounds; CHEMICAL synthesis; REGIOSELECTIVITY (Chemistry); MIGRATION reactions (Chemistry)
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 5, p1279
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201309270