Synlett 2009(12): 1955-1958  
DOI: 10.1055/s-0029-1217519
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© Georg Thieme Verlag Stuttgart ˙ New York

Studies on Fluorinated Annulated Nicotines: Concise Synthesis of cis-4,4-Difluoro-2,3,3a,4,5,9b-hexahydro-1-methyl-1H-pyrrolo[2,3-f]quinoline

Bin Chenga,b, Hongbin Zhai*a,b
a Hefei National Laboratory for Physical Science at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China
b Key Laboratory of Synthetic Chemistry of Natural Substances and State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
e-Mail: +86(21)64166128; e-Mail: zhaih@mail.sioc.ac.cn;
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Received 4 March 2009
Publikationsdatum:
25. Juni 2009 (online)

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Abstract

A fused 6,6,5-tricyclic difluorinated nicotine analogue was efficiently assembled in five steps in 36% overall yield. The conformation-restricting unit is a six-membered fluorinated carbocycle. The gem-difluoromethylene group was introduced through an indium-promoted Barbier allylation of 3-bromo-3,3-difluoropropene. The construction of the tricyclic skeleton was achieved using an intramolecular azomethine ylide-alkene [3+2] cycloaddition.

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