Enantioselective Synthesis of Nicotine via an Iodine-Mediated Hofmann-L?ffler Reaction
An iodine-mediated Hofmann-L?ffler 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.
Del Castillo, Estefanía,Mu?iz, Kilian
supporting information
p. 705 - 708
(2019/02/07)
An improved synthesis of (±)-N#-nitrosonornicotine 5#-acetate
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Marriner, Gwendolyn A.,Kerwin, Sean M.
supporting information; experimental part
p. 2891 - 2892
(2009/09/05)
Simple and versatile synthesis of 1-pyrroline derivatives through thermal rearrangement of N-cyclopropylimines
N-Cyclopropylimines rearrange under thermal conditions to give 1-pyrrolines. The effect of imine and cyclopropane substitution is explored. This methodology allows the presence of different substituents (alkyl, alkenyl, aryl) and the reaction proceeds reg
Campos, Pedro J.,Soldevilla, Alberto,Sampedro, Diego,Rodríguez, Miguel A.
p. 8811 - 8813
(2007/10/03)
Biosynthetic studies of secondary plant metabolites with 13CO2. Nicotiana alkaloids. 2. New synthesis of nornicotine and nicotine. Quantitative carbon-13 NMR spectroscopic analysis of [2',3',N-CH3-13C3]nicotine
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Nakane,Hutchinson
p. 3922 - 3931
(2007/10/04)
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