Journal article
Synthesis and conjugate addition reactions of N-(beta-nitroalkyl)amides
Tetrahedron letters, v 56(48), pp 6722-6725
02 Dec 2015
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Nitration of several di- and trisubstituted alkenes with lithium nitrate/TFAA in nitrile solvents afforded N-(beta-nitroalkyl)amides in 28-72% yields. Nitration of 1,1-diphenylethene gave 1,1-diphenyl-2-nitroethene in 52% yield instead of the N-(beta-nitroalkyl)amide. Reaction of 1-methylcyclohexene using excess lithium nitrate/TFAA in acetonitrile gave a single diastereomer of N-(2,6-dinitro-1-cyclohexyl)acetamide in 55% yield. N-(beta-Nitroalkyl)amides underwent diastereoselective Michael addition to a variety of Michael acceptors. Diastereoselectivity is rationalized on the basis of internal hydrogen-bonding within the intermediate nitronate resulting in a strongly-biased Michael donor conformation. (C) 2015 Elsevier Ltd. All rights reserved.
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Details
- Title
- Synthesis and conjugate addition reactions of N-(beta-nitroalkyl)amides
- Creators
- Peter A. Wade - Drexel UniversityNicholas Paparoidamis - Drexel UniversityJennie Liao - Drexel UniversityBrian C. Manor - University of PennsylvaniaKristine DeBolt - Drexel University
- Publication Details
- Tetrahedron letters, v 56(48), pp 6722-6725
- Publisher
- Elsevier
- Number of pages
- 4
- Grant note
- Drs. Bruce and Cynthia Maryanoff
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- [Retired Faculty]; Chemistry
- Web of Science ID
- WOS:000365060400018
- Scopus ID
- 2-s2.0-84955630680
- Other Identifier
- 991019167716904721
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- Collaboration types
- Domestic collaboration
- Web of Science research areas
- Chemistry, Organic