Enantioselective Additions of Stabilized Carbanions to Imines Generated from α-Amido Sulfones By Using Lipophilic Salts of Chiral Tris(1,2-diphenylethylenediamine) Cobalt(III) Trications as Hydrogen Bond Donor Catalysts

Hemant Joshi, Subrata K. Ghosh, John A. Gladysz*

*Department of Chemistry, Texas A&M University, College Station, TX 77843-3255, Email: gladyszchem.tamu.edu

H. Joshi, S. K. Ghosh, J. A. Gladysz, Synthesis, 2017, 49, 3905-3915.

DOI: 10.1055/s-0036-1590502

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Abstract

An enantiopure hydrogen bond donor catalyst enables an enantioselective addition of dialkyl malonates to Boc-derivatized α-amino sulfones in the presence of K₂CO₃. The diastereomeric salt is similarly applied to additions of nitroalkanes. Precautions to exclude air or moisture are unnecessary.

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Key Words

active methylene compounds, β-amino esters, Werner complexes, cobalt, 1,2-diamine ligands, chiral-at-metal complexes, hydrogen bonding, enantioselective catalysis, chiral benzylic amines, lipophilic anions

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ID: J66-Y2017