2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones

Steven Malcolmson presents the Cu-catalyzed synthesis of 1,2-amino tertiary alcohols.

The development of methods for the enantioselective construction of amines is an important objective in synthetic chemistry, and C–C bond-forming reactions are a critical subset, as highly functionalized molecules may be assembled quickly by the union of two complex fragments. One common tactic utilizes stereoselective nucleophile additions to electrophilic imines; however, there are several families of amines that are not easily prepared in this manner. 1,2-Amino alcohols are one class that are difficult to access via this normal polarity C–C bond formation. In particular, 1,2-amino tertiary alcohols have almost never succumbed to catalytic enantioselective synthesis.

The lab of Professor Steven Malcolmson at Duke University (Durham, USA) envisioned that 1,2-amino tertiary alcohols could be prepared if a nucleophilic α-aminoalkyl transition metal intermediate could be generated and added to a ketone electrophile (reverse polarity strategy).


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