Journal article
Oxidative allene amination for the synthesis of nitrogen-containing heterocycles
ARKIVOC free online journal of organic chemistry, Vol.2018(6), pp.204-233
01/01/2018
DOI: 10.24820/ark.5550190.p010.670
PMCID: PMC6941799
PMID: 31903453
Abstract
The prevalence of stereochemically complex amines in natural products, pharmaceuticals and other bioactive compounds, coupled with the challenges inherent in their preparation, has inspired work to develop new and versatile methodologies for the synthesis of amine-containing stereotriads ('triads'). The key step is a highly chemo-, regio-, and stereo-selective transition-metal catalyzed nitrene transfer reaction that transforms one of the cumulated double bonds of an allene precursor into a bicyclic methyleneaziridine intermediate. This account summarizes our strategies for elaboration of such intermediates into stereochemically rich, densely functionalized amine triads, nitrogen heterocycles, aminated carbocycles and other useful synthetic building blocks.
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Details
- Title: Subtitle
- Oxidative allene amination for the synthesis of nitrogen-containing heterocycles
- Creators
- Josephine Eshon - University of Wisconsin–MadisonNels C. Gerstner - University of Wisconsin–MadisonJennifer M. Schomaker - University of Wisconsin–Madison
- Resource Type
- Journal article
- Publication Details
- ARKIVOC free online journal of organic chemistry, Vol.2018(6), pp.204-233
- DOI
- 10.24820/ark.5550190.p010.670
- PMID
- 31903453
- PMCID
- PMC6941799
- NLM abbreviation
- ARKIVOC
- ISSN
- 1551-7004
- eISSN
- 1551-7012
- Publisher
- Arkat Usa Inc
- Number of pages
- 30
- Grant note
- R01 GM11412 / NIH; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA 517 1254397 / NSF-CAREER; National Science Foundation (NSF); NSF - Office of the Director (OD)
- Language
- English
- Date published
- 01/01/2018
- Academic Unit
- Chemistry
- Record Identifier
- 9984934670302771
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