Journal
ORGANIC LETTERS
Volume 21, Issue 3, Pages 705-708Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03909
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Funding
- Spanish Ministry for Economy and Competitiveness [CTQ2017-88496R]
- FEDER [CTQ2017-88496R]
- CERCA Program of the Government of Catalonia
- COST Action C-H Activation in Organic Synthesis (CHAOS) [CA15106]
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An iodine-mediated Hofmann-Loffler reaction has been developed that enables the first enantioselective synthesis of nicotine based on this synthetic methodology. The effect of the free pyridine core on the involved electrophilic iodine reagents was explored in detail. The final synthesis proceeds under moderate reaction conditions that tolerate the free pyridine core. The same synthetic sequence is also applicable to a number of derivatives with higher substituted pyridine cores, including bipyridine derivatives.
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