Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 46, Pages 15646-15650Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b10799
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Funding
- Stanford University
- National Institutes of Health [R01 GM114061]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM114061] Funding Source: NIH RePORTER
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Herein we report a highly regio- and stereoselective haloazidation of allylic alcohols. This enantioselective reaction uses readily available materials and can be performed on a variety of alkyl-substituted alkenes and can incorporate either bromine or chlorine as the electrophilic halogen component. Both halide and azido groups of the resulting products can be transformed into valuable building blocks with complete stereo specificity. The first example of an enantioselective 1,4-haloazidation of a conjugated diene is reported as well as its application to a concise synthesis of an aza-sugar.
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