Journal article
Fluorinated Amine Stereotriads via Allene Amination
Organic letters, Vol.19(12), pp.3239-3242
06/16/2017
DOI: 10.1021/acs.orglett.7b01342
PMCID: PMC5541934
PMID: 28573862
Abstract
The incorporation of fluorine into organic scaffolds often improves the bioactivity of pharmaceutically relevant compounds. C-F/C-N/C-O stereotriad motifs are prevalent in antivirals, neuraminidase inhibitors, and modulators of androgen receptors, but are challenging to install. An oxidative allene amination strategy using Selectfluor rapidly delivers triply functionalized triads of the form C-F/C-N/C-O, exhibiting good scope and diastereoselectivity for all syn products. The resulting stereotriads are readily transformed into fluorinated pyrrolidines and protected α-, β-, and γ-amino acids.
Details
- Title: Subtitle
- Fluorinated Amine Stereotriads via Allene Amination
- Creators
- Lu Liu - University of Wisconsin–MadisonNels C Gerstner - University of Wisconsin–MadisonLucas J Oxtoby - University of Wisconsin–MadisonIlia A Guzei - University of Wisconsin–MadisonJennifer M Schomaker - University of Wisconsin–Madison
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.19(12), pp.3239-3242
- DOI
- 10.1021/acs.orglett.7b01342
- PMID
- 28573862
- PMCID
- PMC5541934
- NLM abbreviation
- Org Lett
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Grant note
- S10 OD012245 / NIH HHS R01 GM111412 / NIGMS NIH HHS P41 GM103399 / NIGMS NIH HHS S10 RR008438 / NCRR NIH HHS S10 RR029220 / NCRR NIH HHS
- Language
- English
- Date published
- 06/16/2017
- Academic Unit
- Chemistry
- Record Identifier
- 9984934671102771
Metrics
6 Record Views