Journal article
Cyclic nitriles: diastereoselective alkylations
Journal of organic chemistry, v 70(10), pp 3845-3849
13 May 2005
PMID: 15876069
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
[reaction: see text] Diastereoselective alkylations of metalated conformationally locked 4-tert-butylcyclohexanecarbonitrile are highly diastereoselective with magnesium and copper counterions but only modestly diastereoselective with lithium as the counterion. Selective generation of diverse metalated nitriles is readily achieved through bromine-magnesium, -copper, and -lithium exchange reactions of the corresponding bromonitrile or, for lithium, by deprotonating the parent nitrile with lithium diethylamide. Collectively, high alkylation stereoselectivities correlate with the retentive alkylations of C-metalated nitriles, whereas N-lithiated nitriles alkylate with modest selectivity, reflecting minimal steric differences in the corresponding axial and equatorial electrophile trajectories.
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Details
- Title
- Cyclic nitriles: diastereoselective alkylations
- Creators
- Fraser F Fleming - Duquesne UniversitySubrahmanyam Gudipati - Duquesne UniversityZhiyu ZhangWang Liu - Duquesne UniversityOmar W Steward - Duquesne University
- Publication Details
- Journal of organic chemistry, v 70(10), pp 3845-3849
- Publisher
- American Chemical Society; Washington, DC
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000228983300010
- Scopus ID
- 2-s2.0-18744411274
- Other Identifier
- 991020898496104721
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- Web of Science research areas
- Chemistry, Organic