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Chiral Squaramide‐Catalyzed Highly Enantioselective Michael Addition of 2‐Hydroxy‐1,4‐naphthoquinones to Nitroalkenes
Author(s) -
Yang Wen,
Du DaMing
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000981
Subject(s) - squaramide , enantioselective synthesis , michael reaction , chemistry , organocatalysis , catalysis , organic chemistry , combinatorial chemistry
Abstract A chiral squaramide‐organocatalyzed, highly enantioselective Michael addition of 2‐hydroxy‐1,4‐naphthoquinones to nitroalkenes has been developed. This reaction afforded the chiral naphthoquinones in excellent yields (up to 99%) and excellent enantioselectivity (up to 98% ee ) under very low catalyst loading (0.25 mol%). This organocatalytic asymmetric Michael addition provides an efficient alternative route toward the synthesis of chiral functionalized naphthoquinones.