Herein, we report the palladium-catalyzed decarboxylative asymmetric allylic alkylation of α-enaminones. In addition to serving as valuable synthetic building blocks, we exploit the α-enaminone scaffold and its derivatives as probes to highlight structural and electronic factors that govern enantioselectivity in this asymmetric alkylation reaction. Utilizing the (S)-t-BuPHOX ligand in a variety of nonpolar solvents, the alkylated products are obtained in up to 99% yield and 99% enantiomeric excess.
Herein, we report the palladium-catalyzed decarboxylative asymmetric allylic alkylation of α-n class="Chemical">enaminones. In addition to serving as valuable synthetic building blocks, we exploit the α-enaminone scaffold and its derivatives as probes to highlight structural and electronic factors that govern enantioselectivity in this asymmetric alkylation reaction. Utilizing the (S)-t-BuPHOX ligand in a variety of nonpolar solvents, the alkylated products are obtained in up to 99% yield and 99% enantiomeric excess.
Authors: John A Keith; Douglas C Behenna; Justin T Mohr; Sandy Ma; Smaranda C Marinescu; Jonas Oxgaard; Brian M Stoltz; William A Goddard Journal: J Am Chem Soc Date: 2007-09-08 Impact factor: 15.419
Authors: Nathan B Bennett; Douglas C Duquette; Jimin Kim; Wen-Bo Liu; Alexander N Marziale; Douglas C Behenna; Scott C Virgil; Brian M Stoltz Journal: Chemistry Date: 2013-02-27 Impact factor: 5.236
Authors: Douglas C Behenna; Yiyang Liu; Taiga Yurino; Jimin Kim; David E White; Scott C Virgil; Brian M Stoltz Journal: Nat Chem Date: 2011-12-18 Impact factor: 24.427