1373550-38-9Relevant academic research and scientific papers
Stereocontrolled synthesis of vicinal diamines by organocatalytic asymmetric mannich reaction of N -protected aminoacetaldehydes: Formal synthesis of (-)-agelastatin A
Kano, Taichi,Sakamoto, Ryu,Akakura, Matsujiro,Maruoka, Keiji
, p. 7516 - 7520 (2012/06/16)
The 1,2-diamine (vicinal diamine) motif is present in a number of natural products with interesting biological activity and in many chiral molecular catalysts. The efficient and stereocontrolled synthesis of enantioenriched vicinal diamines is still a challenge to modern chemical methodology. We report here both syn- and anti-selective asymmetric direct Mannich reactions of N-protected aminoacetaldehydes with N-Boc-protected imines catalyzed by proline and the axially chiral amino sulfonamide (S)-3. This organocatalytic process represents the first example of a Mannich reaction using Z- or Boc-protected aminoacetaldehyde as a new entry of α-nitrogen functionalized aldehyde nucleophile in enamine catalysis. The obtained optically active vicinal diamines are useful chiral synthons as exemplified by the formal synthesis of (-)-agelastatin A.
