Journal article
[gamma]- and [d]-Hydroxynitriles: diastereoselective electrophile-dependent alkylations
Tetrahedron, v 69(1), pp 366-376
07 Jan 2013
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Deprotonating [gamma]- and [d]-hydroxynitriles with i-PrMgCl allows highly diastereoselective alkylations controlled by the asymmetry of the remote carbinol stereocenter. Mechanistic experiments are consistent with [gamma]-hydroxynitriles alkylating via a chelated magnesiated nitrile whereas [d]-hydroxynitriles favor alkylation from acyclic magnesiated nitriles. Collectively these alkylations; are the first electrophile-dependent alkylations of acyclic nitriles, exhibit a unique influence on the nature of the Grignard used for the deprotonation, and address the challenge of installing quaternary centers in conformationally mobile, acyclic nitriles.
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Details
- Title
- [gamma]- and [d]-Hydroxynitriles: diastereoselective electrophile-dependent alkylations
- Creators
- Robert Mycka - Duquesne UniversityWilliam Eckenhoff - Duquesne UniversityOmar Steward - Duquesne UniversityNathan Barefoot - Duquesne UniversityFraser Fleming - Duquesne University
- Publication Details
- Tetrahedron, v 69(1), pp 366-376
- Publisher
- Elsevier
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000313386100047
- Scopus ID
- 2-s2.0-84870054829
- Other Identifier
- 991020898394104721
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InCites Highlights
Data related to this publication, from InCites Benchmarking & Analytics tool:
- Web of Science research areas
- Chemistry, Organic