Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

Strategy for Stereoselective Metal-free α-Functionalization of 2-Azaaryl Acetates with N-Boc Imines

Strategy for Stereoselective Metal-free α-Functionalization of 2-Azaaryl Acetates with N-Boc Imines
Marcos San Segundo, Iñaki Bastida, Rosa López, Claudio Palomo
We report the first diastereo- and enantioselective formal Mannich reaction of 2-pyridyl acetates which gives rise to α- and β-functionalized 2-substituted pyridines. Key for success is the previous azaarene N-oxide formation enabling α-carbon deprotonation by a mild bifunctional Brønsted base and subsequent reaction with N-Boc imines under almost perfect stereocontrol. An effective couple: The combined use of 2-pyridyl N-oxide acetates, as pyridyl acetate surrogates, and ureidopeptide-based Brønsted bases enables the synthesis of orthogonally protected α- and β-functionalized 2-substituted pyridines which, to date, have been elusive through catalytic approaches

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201703748

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