Journal article
Electrophile-Dependent Alkylations of Lithiated 4-Alkoxyalk-4-enenitriles
Journal of organic chemistry, v 83(5), pp 2753-2762
02 Mar 2018
PMID: 29432696
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Alkylations of acyclic, lithiated 4-alkoxyalk-4-enenitriles are highly diastereoselective with an unusual electrophile-dependent preference. Alkyl halides, sulfur, chlorine, and acyl cyanide electrophiles intercept a series of lithiated 4-alkoxyalk-4-enenitriles to install contiguous tertiary-quaternary stereocenters with high diastereoselectivity, whereas acylations with ester and carbonate electrophiles are modestly selective. The diastereoselectivity is consistent with electrophilic attack on the most accessible face of the lithated nitrile for most electrophiles except ester and carbonate electrophiles, which likely precoordinate the lithiated nitrile before acylation. Intercepting the lithiated 4-alkoxyalk-4-enenitriles with a range of electrophiles provide insight into the criteria for otherwise challenging diastereoselective alkylations and acylations of acyclic nitriles.
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Details
- Title
- Electrophile-Dependent Alkylations of Lithiated 4-Alkoxyalk-4-enenitriles
- Creators
- Bhaskar R. Pitta - Biophore India , Hyderabad, Telangana 500033, India.Omar W. Steward - Duquesne UniversityFraser F. Fleming - Drexel University
- Publication Details
- Journal of organic chemistry, v 83(5), pp 2753-2762
- Publisher
- American Chemical Society; Washington, DC
- Number of pages
- 10
- Grant note
- 0515715; CHE 1464494 / NSF; National Science Foundation (NSF) 1464494 / Division Of Chemistry; National Science Foundation (NSF); NSF - Directorate for Mathematical & Physical Sciences (MPS)
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000426803300025
- Scopus ID
- 2-s2.0-85043256134
- Other Identifier
- 991019168720704721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Organic