A Simple Route to Chiral Synthesis

A Simple Route to Chiral Synthesis

Author: Claire D'Andola

Asymmetric synthesis of all-carbon quaternary stereogenic centers presents a significant challenge in organic synthesis and has attracted much interest over the last decade. One of the many synthetic solutions disclosed in the literature are rhodium and copper-catalyzed asymmetric conjugate additions (ACAs) using organometallic reagents. However, despite their synthetic potential, only a few metal-catalyzed ACA reactions have been reported for alkenyl nucleophiles to generate quaternary stereogenic centers.

Alexandre Alexakis and Daniel Müller, University of Geneva, Switzerland, have described the asymmetric copper-catalyzed conjugate addition of alkenylaluminum reagents to 3-substituted cyclic enones to form stereogenic all-carbon quaternary centers.

A large number of alkenyl nucleophiles can undergo the copper-catalyzed ACA with good to very good levels of enantioselectivity, typically 70–90 % ee, when cyclohexenones and derivatives are used as the substrate.

The reaction protocols are practical and the ligand and copper salt used are relatively inexpensive.

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