Hydrogen Bond Catalyzed Aza-Henry Reactions

Scheme 6.10 Aza-Henry reactions catalyzed by polar ionic hydrogen-bonding.

Aza-Henry Reaction Catalyzed by Polar Ionic Hydrogen Bonding [15] (p. 221)... 

A purely ionic hydrogen bond activation mechanism might be involved in the aza-Henry reaction between a-iminoesters, a very reactive subclass of imines, and various nitroalkanes catalyzed by the BINOL phosphoric acid 44 [54]. The corresponding P-nitro-a-amino acid esters were produced in good yields, diastereo- and enantioselectivities (Scheme 29.23). The authors postulated a dual role of catalyst 44 through activation of the a-iminoester by protonation and control over the nitroaUcane/nitronate equilibrium (Scheme 29.24). 

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