Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 5, Pages 3851-3855Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c03056
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Funding
- National Science Foundation (NSF-CHE) [1904530]
- Department of Defense (DOD-CDMRP) [W81XWH-16-1-0699]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1904530] Funding Source: National Science Foundation
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The article presents a method for transforming simple aryl halides into highly functionalized intermediates, which can then be converted to valuable compounds.
The gamma-amino-alpha-aryl alcohol is a key functional group for the design of inhibitors directed toward a critical family of metabolic enzymes. Here we report the transformation of simple aryl halides to a highly functionalized benzyl (3-oxo-3-arylpropyl)-carbamate intermediate that can rapidly be converted to a high value gamma-amino-alpha-aryl alcohol. This chemistry is realized through a two-step process involving an enamine-based Heck coupling (EBHC) followed by a one-pot catalytic Cbz-deprotection and ketone reduction of EBHC products.
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