Premium
Stereocontrolled Construction of 3,4‐Dihydrocoumarin Scaffolds with a Quaternary Amino Acid Moiety via Chiral Squaramide‐Catalyzed Cascade Michael Addition/Lactonization Reaction
Author(s) -
Wang Yuehua,
Pan Jianping,
Jiang Rongrong,
Wang Youming,
Zhou Zhenghong
Publication year - 2016
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.201500862
Subject(s) - squaramide , moiety , chemistry , michael reaction , cascade reaction , stereochemistry , tandem , phenols , catalysis , enantioselective synthesis , organocatalysis , combinatorial chemistry , organic chemistry , materials science , composite material
An asymmetric tandem Michael addition–lactonization between ortho ‐nitrovinylphenols and azalactones was investigated for constructing 3,4‐dihydrocoumarin backbones with a quaternary amino acid moiety. Under the catalysis of the chiral squaramide derived from L ‐ tert ‐leucine, a wide range of substituted ( E )‐2‐(2‐nitrovinyl)phenols and azalactones were well tolerated in this tandem reaction to provide the corresponding biologically significant 3,4‐dihydrocoumarin derivatives in excellent yields with high levels of diastereo‐ and enantioselectivity.