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Asymmetric aza-Henry reaction of chiral fluoroalkyl α,β-unsaturated N-tert-butanesulfinylketoimines: an efficient approach to enantiopure fluoroalkylated α,β-diamines and α,β-diamino acids†
Fan Zhang,Zhen-Jiang Liu,Jin-Tao Liu
Organic & Biomolecular Chemistry Pub Date : 03/23/2011 00:00:00 , DOI:10.1039/C1OB05132F
Abstract

The aza-Henry reaction of chiral fluoroalkyl α,β-unsaturated N-tert-butanesulfinyl ketoimines and nitromethane was achieved in the presence of 0.2 equivalent of anhydrous potassium carbonate to give the corresponding adducts diastereoselectively in high yields. Transformations which highlighted the synthetic potential of these aza-Henry adducts were also performed.

Graphical abstract: Asymmetric aza-Henry reaction of chiral fluoroalkyl α,β-unsaturated N-tert-butanesulfinyl ketoimines: an efficient approach to enantiopure fluoroalkylated α,β-diamines and α,β-diamino acids
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