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Accepted (AM)Open Access (License Unspecified), Open
Journal article
Metalated nitriles: SNi′ cyclizations with a propargylic electrophile
Tetrahedron letters, v 56(23), pp 3216-3219
03 Jun 2015
PMID: 26120212
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
A rare 5-exo-dig S
N
i′ cyclization with magnesiated and lithiated nitriles affords a
cis-
fused hydrindane bearing an exocyclic allene. The cyclization of the dilithiated nitrile pits a stereoelectronic preference for a
trans-
hydrindane against a cyclization through a less strained transition structure to the corresponding
cis
-hydrindane. Computational modeling suggests that the dilithiated nitrile cyclizes to a
cis-
hydrindane because the preferred transition structure positions the lithium cation in a cone of electron density that bridges the nitrile-bearing carbon, an alkoxide, and an electron-rich alkyne functionality.
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Details
- Title
- Metalated nitriles: SNi′ cyclizations with a propargylic electrophile
- Creators
- Ping Lu - Duquesne UniversityVenkata S. Pakkala - Duquesne UniversityJeffrey D. Evanseck - Duquesne UniversityFraser F. Fleming - Duquesne University
- Publication Details
- Tetrahedron letters, v 56(23), pp 3216-3219
- Publisher
- Elsevier
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000356544800060
- Scopus ID
- 2-s2.0-84929600797
- Other Identifier
- 991020898500804721
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InCites Highlights
Data related to this publication, from InCites Benchmarking & Analytics tool:
- Web of Science research areas
- Chemistry, Organic