Alicyclic-Amine-Derived Imine-BF3 Complexes: Easy-to-Make Building Blocks for the Synthesis of Valuable α-Functionalized Azacycles
Subhradeep Dutta
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
These authors contributed equally to this work.
Search for more papers by this authorDr. Jae Hyun Kim
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
College of Pharmacy, Chung-Ang University, Seoul, 06974 Republic of Korea
These authors contributed equally to this work.
Search for more papers by this authorKamal Bhatt
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
Search for more papers by this authorDillon R. L. Rickertsen
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
Search for more papers by this authorDr. Khalil A. Abboud
Center for X-ray Crystallography, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
Search for more papers by this authorDr. Ion Ghiviriga
Center for NMR Spectroscopy, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Daniel Seidel
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
Search for more papers by this authorSubhradeep Dutta
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
These authors contributed equally to this work.
Search for more papers by this authorDr. Jae Hyun Kim
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
College of Pharmacy, Chung-Ang University, Seoul, 06974 Republic of Korea
These authors contributed equally to this work.
Search for more papers by this authorKamal Bhatt
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
Search for more papers by this authorDillon R. L. Rickertsen
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
Search for more papers by this authorDr. Khalil A. Abboud
Center for X-ray Crystallography, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
Search for more papers by this authorDr. Ion Ghiviriga
Center for NMR Spectroscopy, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Daniel Seidel
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611 USA
Search for more papers by this authorAbstract
A new strategy to access α-functionalized alicyclic amines via their corresponding imine-BF3 complexes is reported. Isolable imine-BF3 complexes, readily prepared via dehydrohalogenation of N-bromoamines in a base-promoted/18-crown-6 catalyzed process followed by addition of boron trifluoride etherate, undergo reactions with a wide range of organometallic nucleophiles to afford α-functionalized azacycles. Organozinc and organomagnesium nucleophiles add at ambient temperatures, obviating the need for cryogenic conditions. In situ preparation of imine-BF3 complexes provides access to α-functionalized morpholines and piperazines directly from their parent amines in a single operation. α-Functionalized morpholines can be elaborated further, for instance by installing a second substituent in the α′-position.
Open Research
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