Premium
Highly Enantioselective Organocatalytic Michael Addition of 2‐Hydroxy‐ 1,4‐naphthoquinone to β,γ‐Unsaturated α‐Oxo Esters
Author(s) -
Wang YiFeng,
Zhang Wei,
Luo ShuPing,
Zhang GuangCun,
Xia AiBao,
Xu XiangSheng,
Xu DanQian
Publication year - 2010
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.201000885
Subject(s) - enantioselective synthesis , chemistry , michael reaction , bifunctional , organocatalysis , amine gas treating , adduct , organic chemistry , optically active , naphthoquinone , combinatorial chemistry , catalysis
An organocatalytic enantioselective Michael addition of 2‐hydroxy‐1,4‐naphthoquinone to β,γ‐unsaturated α‐oxo esters has been developed. The process was promoted by bifunctional chiral amine derived squaramides according to a hydrogen‐bonding mediated activation mechanism and afforded the chiral adducts in high yields (up to 88 %) and excellent enantioselectivity (up to 98 % ee ) under mild conditions. This organocatalytic asymmetric Michael addition provides an efficient route toward the synthesis of optically active functionalized naphthoquinones.