Enantioselective Fluoroamination: 1,4-Addition to Conjugated Dienes Using Anionic Phase-Transfer Catalysis†
Hunter P. Shunatona
Department of Chemistry, University of California—Berkeley, Latimer Hall, Berkeley, CA (USA)
Search for more papers by this authorNatalja Früh
Department of Chemistry, University of California—Berkeley, Latimer Hall, Berkeley, CA (USA)
Search for more papers by this authorYi-Ming Wang
Department of Chemistry, University of California—Berkeley, Latimer Hall, Berkeley, CA (USA)
Search for more papers by this authorDr. Vivek Rauniyar
Department of Chemistry, University of California—Berkeley, Latimer Hall, Berkeley, CA (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. F. Dean Toste
Department of Chemistry, University of California—Berkeley, Latimer Hall, Berkeley, CA (USA)
Department of Chemistry, University of California—Berkeley, Latimer Hall, Berkeley, CA (USA)Search for more papers by this authorHunter P. Shunatona
Department of Chemistry, University of California—Berkeley, Latimer Hall, Berkeley, CA (USA)
Search for more papers by this authorNatalja Früh
Department of Chemistry, University of California—Berkeley, Latimer Hall, Berkeley, CA (USA)
Search for more papers by this authorYi-Ming Wang
Department of Chemistry, University of California—Berkeley, Latimer Hall, Berkeley, CA (USA)
Search for more papers by this authorDr. Vivek Rauniyar
Department of Chemistry, University of California—Berkeley, Latimer Hall, Berkeley, CA (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. F. Dean Toste
Department of Chemistry, University of California—Berkeley, Latimer Hall, Berkeley, CA (USA)
Department of Chemistry, University of California—Berkeley, Latimer Hall, Berkeley, CA (USA)Search for more papers by this authorWe would like to thank the University of California at Berkeley for funding and David S. Tatum for X-ray crystallography analysis.
Graphical Abstract
Chiral-anion phase-transfer catalysis (PTC) has been applied towards the enantioselective fluorocyclization reactions of 1,3-dienes. The method affords unprecedented fluorinated benz[f]isoquinoline and octahydroisoquinoline products in high yields and up to 96 % ee. New fluorinated amine reagents outperformed Selectfluor in the desired transformation.
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