Premium
Palladium‐Catalyzed Synthesis of Substituted Cycloheptane‐1,4‐diones by an Asymmetric Ring‐Expanding Allylation (AREA)
Author(s) -
Schulz Sabrina R.,
Blechert Siegfried
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200604553
Subject(s) - aldol reaction , cycloheptane , heptane , palladium , chemistry , catalysis , cycloaddition , bicyclic molecule , ketone , ring (chemistry) , enantioselective synthesis , stereochemistry , medicinal chemistry , organic chemistry
The right AREA : Functionalized, seven‐ and eight‐membered carbocycles are available from an asymmetric Pd‐catalyzed decarboxylative fragmentation of strained bicyclo[3.2.0]heptane‐2‐ones (see scheme, dba= trans , trans ‐dibenzylideneacetone). The products were formed in a sequence of [2+2] cycloaddition, retro‐aldol reaction, and asymmetric allylation of ketone enolates.