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Journal article
Carbon-Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols
Organic letters, Vol.19(10), pp.2630-2633
05/19/2017
PMID: 28467706
Web of Science ID: WOS:000402023500044
Abstract
A vanadium catalyzed 1,3-rearrangement of allenols to form transient vanadium enolates that selectively couple with electrophilic nitrogen sources is reported even in the presence of competing simple protonation and Alder-ene pathways. Hydrazine products can be cyclized in a 6-endo-trig fashion which, upon reductive cleavage of the N-N bond, yield 1,4-diamines. Additionally, cleavage of the N-N bond before cyclization can be achieved to form beta-hydroxy amines, a common structural motif of biologically active compounds.
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Details
- Title
- Carbon-Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols
- Publication Details
- Organic letters, Vol.19(10), pp.2630-2633
- Resource Type
- Journal article
- Publisher
- American Chemical Society
- Number of pages
- 4
- Grant note
- R01GM033049 / NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Institute of General Medical Sciences (NIGMS) John Stauffer Memorial Fellowship
- Copyright
- © 2017 American Chemical Society
- Identifiers
- WOS:000402023500044; 99381709174506600
- Academic Unit
- Chemistry; Hal Marcus College of Science and Engineering
- Language
- English