Brief Surveys

Figure 1. Taken from [1].

This article illustrates the synthetic uses of linear N-Chloramines (Figure 1) [1]. Upon the treatment of a suitable base, the resultant azaallyl ions are capable to carry out cycloadditions to give useful pyrrolidine scaffolds. The azaallyl ion is also a disguise for an imine, which has the potential to carry out useful allylation reactions. It is intriguing to note that certain bases do not work well for these N-chloramines, as suggested by the workers.

Another one on the same issue of Tetrahedron Letters. Ever think of using chiral azo compounds (yes – that azo dye you have encountered in A-Level) to synthesize enantiopure amino acids (Figure 2, 3) [2]?


Figure 2. Taken from [2].


Figure 3. Taken from [2].

Reference:
1. Preparation of 2-azaallyl anions and imines from N-chloroamines and their cycloaddition and allylation
Shveta Pandiancherri, David W. Lupton
Tetrahedron Letters 52 (2011) 671–674

2. Chiral azo compounds: enantioselective synthesis and transformations into
β-amino alcohols and α-amino acids with a quaternary stereocenter
Friedrich R. Dietz, Agnes Prechter, Harald Gröger, Markus R. Heinrich
Tetrahedron Letters 52 (2011) 655–657