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Silylative Reductive Amination of α,β‐Unsaturated Aldehydes: A Convenient Synthetic Route to β‐Silylated Secondary Amines
Author(s) -
Kim Eunae,
Park Sehoon,
Chang Sukbok
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800958
Subject(s) - reductive amination , chemistry , hydrosilylation , regioselectivity , steric effects , catalysis , borane , amination , silylation , amine gas treating , organic chemistry , frustrated lewis pair , cascade reaction , combinatorial chemistry , organocatalysis , lewis acids and bases , enantioselective synthesis
Described here is a reductive amination/hydrosilylation cascade of α,β‐unsaturated aldehydes mediated by a Lewis acidic borane catalyst. The present reaction system provides an one‐pot synthetic route towards β‐silylated secondary amines that have not been accessible by other previous catalysis. Comparative 1 H NMR studies on the silylative reduction of enimines revealed that steric bulkiness of primary amine reactants strongly affects both catalytic efficiency and regioselectivity. This strategy was applicable to a broad range of substrates and amenable to one‐pot gram‐scale synthesis. Moreover, a diastereoselective introduction of the β‐silyl group was also found to be feasible (d.r. up to 71:29).