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Tandem Iminium/Copper Catalysis: Highly Enantioselective Synthesis of α,β‐Disubstituted Aldehydes
Author(s) -
Kim JuHye,
Park EunJin,
Lee HwaJung,
Ho XuanHuong,
Yoon HyoSang,
Kim Pilsoo,
Yun Hoseop,
Jang HyeYoung
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300333
Subject(s) - iminium , chemistry , enantioselective synthesis , nitromethane , piperidine , copper , catalysis , aldehyde , organocatalysis , organic chemistry , combinatorial chemistry , tandem , materials science , composite material
With the goal of synthesizing biologically and synthetically valuable products under environmentally benign and economic conditions, an asymmetric organocatalytic reaction was combined with a copper catalytic reaction. This iminium/copper catalysis allowed highly optically active α,β‐disubstituted aldehydes to be synthesized with good yields in one‐pot fashion. The β‐substitution took place through iminium‐catalyzed Michael addition of nitromethane or diethyl malonate to the α,β‐unsaturated aldehydes, followed by copper‐assisted addition of TEMPO (2,2,6,6‐tetramethylpiperidin‐1‐yloxyl) at the aldehyde α‐position. An iminium/copper‐catalyzed tandem addition product was converted into a 3,4,5‐trisubstituted piperidine for X‐ray crystallographic analysis.