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Enantioselective Catalytic Domino Aza‐Michael–Henry Reactions: One‐Pot Asymmetric Synthesis of 3‐Nitro‐1,2‐dihydroquinolines via Iminium Activation
Author(s) -
Luo Hao,
Yan Xilong,
Chen Ligong,
Li Yang,
Liu Na,
Yin Guohui
Publication year - 2016
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.201501618
Subject(s) - iminium , enantioselective synthesis , chemistry , nitro , nitroaldol reaction , domino , michael reaction , organocatalysis , cascade reaction , yield (engineering) , catalysis , medicinal chemistry , organic chemistry , alkyl , materials science , metallurgy
Asymmetric transformations arising from iminium activation of aromatic aldehydes are uncommon. In this work, an enantioselective organocatalytic domino aza‐Michael–Henry reaction between N ‐(2‐formylphenyl)sulfonamides and trans ‐β‐nitro olefins through iminium activation has been presented. This reaction proceeded smoothly to give chiral 3‐nitro‐1,2‐dihydroquinolines in high yields with up to 88 % ee under mild conditions. Furthermore, a preliminary study showed that 2‐mercaptobenzaldehyde derivatives could participate in a thia‐Michael–Henry reaction with trans ‐β‐nitro olefins to yield chiral 3‐nitro‐2 H ‐thiochromenes.