180347-79-9Relevant academic research and scientific papers
82. Enantioselective reduction of electrophilic C=C bonds with sodium tetrahydroborate and 'semicorrin' cobalt catalysts
Misun, Marian,Pfaltz, Andreas
, p. 961 - 972 (1996)
'Semicorrin' cobalt complexes, prepared in situ from cobalt(II) chloride and the corresponding ligands, are efficient catalysts for the enantioselective reduction of electrophilic C=C bonds with NaBH4. The best selectivities (> 90% ee) are achieved with α,β-unsaturated carboxamides and carboxylates. Analogous α,β-unsaturated nitriles, sulfones, and phosphonates afford enantiomenc excesses of 50-70%. Interestingly, in the reduction of α,β-unsaturated sulfones, the highest enantioselectivities were obtained with unsymmetrical 'semicorrins', whereas in all other cases C2-symmetric 'semicorrins' proved to be superior.
