Catalytic Enantioselective Synthesis of N,Cα,Cα-Trisubstituted α-Amino Acid Derivatives Using 1H-Imidazol-4(5H)-ones as Key Templates†
Julen Etxabe
Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorJoseba Izquierdo
Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorDr. Aitor Landa
Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorProf. Mikel Oiarbide
Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorCorresponding Author
Prof. Claudio Palomo
Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018 San Sebastián (Spain)Search for more papers by this authorJulen Etxabe
Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorJoseba Izquierdo
Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorDr. Aitor Landa
Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorProf. Mikel Oiarbide
Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorCorresponding Author
Prof. Claudio Palomo
Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018 San Sebastián (Spain)Search for more papers by this authorFinancial support was provided by the University of the Basque Country UPV/EHU (UFI 11/22), Basque Government (Grant No IT-628-13 and Saiotek 2014), and Ministerio de Economía y Competitividad (MEC, Grant CTQ2013-47925-C2-1-P), Spain. J.E. thanks MEC and J.I. thanks UPV/EHU for Fellowships. We also thank SGIker (UPV/EHU) for providing NMR, HRMS, and X-Ray resources.
Graphical Abstract
A BB method: 1H-imidazol-4(5H)-ones serve as effective and easily available α-amino acid surrogates for the catalytic and highly diastereo- and enantioselective direct construction of N-substituted quaternary α-amino acid derivatives. The reaction is catalyzed by a Brønsted base (BB) and proceeds with different Michael acceptors. EWG=electron-withdrawing group.
Abstract
1H-Imidazol-4(5H)-ones are introduced as novel nucleophilic α-amino acid equivalents in asymmetric synthesis. These compounds not only allow highly efficient construction of tetrasubstituted stereogenic centers, but unlike hitherto known templates, provide direct access to N-substituted (alkyl, allyl, aryl) α-amino acid derivatives.
Supporting Information
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