Abstract
The α-regioselectivity of carbonyl crotylation is a long-standing problem in the realm of C–C bond formation reactions. We demonstrate that zinc-mediated crotylation of aldehydes and ketones can afford α-linear homoallylic alcohols exclusively to provide a simple solution for this problem. In this context, we describe a method for the α-regioselective crotylation of aldehydes and ketones by using an easily available starting material, such as crotyl bromide, zinc dust, and the less-toxic solvent DMPU. The reaction has broad substrate scope and is highly efficient. Moreover, a metallo-[3,5]-sigmatropic rearrangement is proposed to account for the high α-regioselectivity in the zinc-mediated crotylation.
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