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Asymmetric Construction of Quaternary Stereocenters: Synthesis of Enantiopure Amino Acid‐Based Tricyclic α,β‐Enones through an ipso ‐Friedel–Crafts/Michael Addition Cascade
Author(s) -
RodríguezSolla Humberto,
Concellón Carmen,
Tuya Paula,
GarcíaGranda Santiago,
Díaz M. Rosario
Publication year - 2012
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.201100497
Subject(s) - enantiopure drug , chemistry , friedel–crafts reaction , stereocenter , michael reaction , phosphoric acid , tricyclic , cascade , boron trifluoride , stereochemistry , cascade reaction , organic chemistry , enantioselective synthesis , catalysis , chromatography
An efficient reaction of the (2 R ,1′ S )‐ or (2 S ,1′ S )‐ N,N ‐bis( p ‐methoxybenzyl)‐2‐(1‐aminoalkyl)epoxides, derived from α‐amino acids, with boron trifluoride‐phosphoric acid complex is described. This process affords highly elaborated enantiopure tricyclic α,β‐enones in high yields, through an ipso ‐Friedel–Crafts/Michael addition cascade.