Abstract

AbstractThe 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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