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Chiral Squaramides as Highly Enantioselective Catalysts for Michael Addition Reactions of 4‐Hydroxycoumarins and 4‐Hydroxypyrone to β,γ‐Unsaturated α‐Keto Esters
Author(s) -
Xu DanQian,
Wang YiFeng,
Zhang Wei,
Luo ShuPing,
Zhong AiGuo,
Xia AiBao,
Xu ZhenYuan
Publication year - 2010
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.201000094
Subject(s) - enantioselective synthesis , michael reaction , chemistry , catalysis , organocatalysis , computer science , addition reaction , organic chemistry , combinatorial chemistry
Distance brings forth beauty : The first highly enantioselective organocatalytic Michael addition of 4‐hydroxycoumarins and the analogous 4‐hydroxy‐6‐methyl‐2‐pyrone to β,γ‐unsaturated α‐keto esters by using chiral squaramides as the organocatalysts is disclosed. The efficiency of the process is attributed to the hydrogen‐bonding activation (see scheme).