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An Asymmetric Organocatalytic Quadruple Cascade Initiated by a Friedel–Crafts‐Type Reaction with Electron‐Rich Arenes
Author(s) -
Erdmann Nico,
Philipps Arne R.,
Atodiresei Iuliana,
Enders Dieter
Publication year - 2013
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.201201099
Subject(s) - chemistry , friedel–crafts reaction , stereocenter , cascade reaction , moiety , organocatalysis , domino , aniline , trimethylsilyl , organic chemistry , catalysis , enantioselective synthesis , combinatorial chemistry
An organocatalytic quadruple domino reaction initiated by a Friedel–Crafts‐type reaction of electron‐rich arenes is described. The procedure involving up to three different Michael acceptors afforded highly functionalized cyclohexenecarbaldehydes bearing an aniline moiety, which are of great pharmaceutical and agricultural interest. This diphenylprolinol trimethylsilyl ether‐catalyzed reaction also generates up to 4 contiguous stereocenters. It could be shown that various functional groups are tolerated and all products were obtained with very good diastereo‐ and excellent enantioselectivity.