Premium
Asymmetric Synthesis of Dihydrofurans via Organocatalytic Domino Michael–Alkylation Reaction
Author(s) -
Feng Juhua,
Lin Lili,
Yu Kunru,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2015
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.201401198
Subject(s) - chemistry , stereocenter , bicyclic molecule , desymmetrization , alkylation , yield (engineering) , organocatalysis , domino , dimedone , cyclohexane , michael reaction , enantioselective synthesis , cascade reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
The chiral N , N′ ‐dioxide C‐PrPr 2 has been developed as an efficient organocatalyst to catalyze the asymmetric domino Michael–alkylation reaction between cyclohexane‐1,3‐dione derivatives and bromonitrostyrenes. For dimedone, the corresponding bicyclic 2,3‐dihydrofurans with two stereocenters were obtained in up to 99 % yield with 95:5 d.r. and 96 % ee . For prochiral 5‐monosubstituted cyclohexane‐1,3‐diones, the desymmetrization reaction provided the bicyclic 2,3‐dihydrofurans with three stereocenters in up to 90 % yield with 82:18 d.r. and 94 % ee .