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Recently, a Cu-catalyzed asymmetric conjugate addition of Grignard reagents to enals with modest selectivities and yields was described. See
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See the Supporting Information
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See the Supporting Information.
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As the substrate is a racemic chloroacetate, it is probable that in situ racemization of the starting material or isomerization of the copper intermediate occurs during slow addition of the Grignard reagent. Because of the high sensitivity of the in situ-formed chloroacetate, to date it has not been possible to monitor the ee of the substrate during the reaction (kinetic resolution)
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As the substrate is a racemic chloroacetate, it is probable that in situ racemization of the starting material or isomerization of the copper intermediate occurs during slow addition of the Grignard reagent. Because of the high sensitivity of the in situ-formed chloroacetate, to date it has not been possible to monitor the ee of the substrate during the reaction (kinetic resolution).
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It has been shown that the regioselectivity of the copper-catalyzed addition of MeMgBr to cinnamyl-type allylic chlorides is lower than for other alkyl Grignard reagents. See
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