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Cy‐SaBOX/Copper(II)‐Catalyzed Highly Diastereo‐ and Enantioselective Synthesis of Bicyclic N,O Acetals
Author(s) -
Liu QiongJie,
Wang Lijia,
Kang QiKai,
Zhang X. Peter,
Tang Yong
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201603911
Subject(s) - bicyclic molecule , enantioselective synthesis , catalysis , copper , chemistry , combinatorial chemistry , reaction conditions , crystal structure , organic chemistry
Facile and effective access for the asymmetric construction of the useful and important skeleton of the bicyclic N,O‐acetals is described. Cu II /SaBOX could catalyze the reaction of β,γ‐unsaturated α‐ketoesters with cyclic enamines efficiently, thus affording the desired products in excellent yields with excellent stereoselectivities (21 examples; up to 99 % yields; up to >95:5 d.r.; and 95–99 % ee ). This reaction can be well performed on gram scale, even with only 1 mol % catalyst loading. The single‐crystal structures of the copper complexes lead to a good understanding of the stereo‐synergistic effects of the sidearm.