Azetidine-2-carbonitriles

R. erythropolis (previously R. rhodochrous) AJ270, which has been utilized in many enantioselective transformations of nitriles such as cyclopropane, oxirane, and aziridine analogs [10, 12], was recently proved to catalyze the enantioselective hydrolysis of azetidine-2-carbonitriles [13] and P-lactam carbonitriles also [14] (Figure 11.2). Carboxylic acids and carboxamides were also obtained with significant enantiomeric excesses from 3-hydroxy-4-aryloxybutanenitriles and 3-hydroxy-3-arylpropanenitriles (Figure 11.3) using R. rhodochrous ATCC BAA-870 [15], which is more elaborately discussed in Chapter 14. 

Figure 11.2 Biotransformations of racemic azetidine-2-carbonitriles and 3-lactam carbonitriles by nitrile hydratase and amidase in whole cells of Rhodococcus erythropolis A]270 [13]. The nitrile hydratase is not...

D.-H. Leng, D.-X. Wang, J. Pan, Z.-T. Huang, M.-X. Wang, Highly efficient and enantioselec-tive biotransformations of racemic azetidine-2-carbonitriles and their synthetic applications,... 

R. erythropolis AJ270 (4-Oxo)Azetidine-2-carbonitriles Enantiopure (4-oxo)azetidine-2-carboxylic acids and carboxamides Chemoenzymatic synthesis of various building blocks [105,106]... 

Azete, tris-dimethylamino-, structure, calculation, synthesis, 56, 356 Azetidine carbonitrile oxides, vinyl-, intramolecular cycloadditions, 60,... 

The first application of Baylis-Hillman adducts in the synthesis of azetidines has also been described. The synthesis involved an eiScient, one-pot and highly diastereoselective annulation of the unmodified Baylis-Hillman adduct (63) involving A -arylphosphoramidate (64) to afford 1,2-disubstituted azetidine-3-carbonitrile (65) (Scheme 21). 

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