Asymmetric synthesis of 3,3-diarylpropanals with chiral diene-rhodium catalysts.
A general route to enantioenriched 3,3-diarylpropanals is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to cinnamaldehyde derivatives in the presence of chiral dienes. The addition of both electron-poor as well as electron-rich boronic acids proceeds smoothly with various enals in 63-90% yield with high enantioselectivities (89-93% ee).
Paquin
Jean-François
JF
Laboratorium für Organische Chemie, ETH Hönggerberg, CH-8093 Zürich, Switzerland.
Defieber
Christian
C
Stephenson
Corey R J
CR
Carreira
Erick M
EM