Abstract
AbstractThe enantioselective desymmetrizing C−H activation of α‐gem‐dialkyl acyclic amides remains challenging because the availability of four chemically identical unbiased methylene C(sp3)−H bonds and increased rotational freedoms of the acyclic systems add tremendous difficulties for chemo‐ and stereocontrol. We have developed a method for the synthesis of acyclic aliphatic amides with α,β‐contiguous stereogenic centers via PdII‐catalyzed asymmetric arylation of unbiased methylene C(sp3)−H, in good yields and with high levels of enantio‐, chemo‐ and diastereoselectivity (up to >99 % ee and >20:1 d.r.). Successive application of this method enables the sequential arylation of the gem‐dialkyl groups with two different aryl iodides, giving a range of β‐Ar1‐β′‐Ar2‐aliphatic acyclic amides containing three contiguous stereogenic centers with excellent diastereoselectivity.
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