Journal
ORGANIC LETTERS
Volume 20, Issue 22, Pages 7253-7256Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03168
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Funding
- University of Minnesota
- American Chemical Society's Petroleum Research Fund (PRF) [56505-DNI1]
- National Institute of General Medical Sciences of the National Institutes of Health [R35GM124718]
- NIH [S10OD011952]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R35GM124718] Funding Source: NIH RePORTER
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The first detailed description of the catalytic racemization of activated benzylic and allylic azides under mild conditions is reported. A kinetic analysis of the observed racemization indicates a first-order dependence on azide, a first-order dependence on catalyst, and that the rate of racemization correlates to sigma(+) A variety of azides with varying substitution patterns undergo facile racemization, and catalyst selection can tune this process.
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