Bruylants reaction

A new diastereoselective route to aromatic cw-erythrinanes represents the combined intramolecular Strecker and Bruylants reactions of the phenethyl-cyclohexanylethylamines 88 (Scheme 11). Deprotection of the carbonyl function and addition of potassium cyanide causes the Strecker reaction to give the angularly substituted hydroindole derivatives 89 in nearly quantitative yields. Then the Bruylants reaction is... 

Reimann E, Ettmayr C (2004) An Improved Stereocontrolled Route to m-Erythri-nanes by Combined Intramolecular Streckerand Bruylants Reaction. Monatsh Chem 135 1143... 

Allylamines have received much attention in the recent literature, a trend which appears to be continuing. a-sec-Allylamines have been rarely reported but a recent disclosure describes their syn-thesis via application of the Bruylants reaction. The method is versatile in that either enals can be converted to vinyl amino-nitriles prior to reaction with a Grignard reagent, or vinyl Grignard reagents can be reacted with a-aminonitriles (Scheme 15). Yields of the products were moderate to good. 

For instance, a Strecker reaction followed by hydrolysis can lead to the oxetane amino acid the intermediate cyanoamine can also be used in a Bruylants reaction to access 3-amino-3-aryloxetanes (Scheme 18.25). Oxetan-3-one can also be converted into an activated Michael acceptor via Wittig or Horner-Wadworth Emmons reactions (Scheme 18.26). ° ... 

The hydrolysis of diamides has been studied by Bruylants et al.178t258t259, who found that, for complete hydrolysis, the reaction may be looked at as a sequence of two consecutive-competitive reactions, viz. 

Poupaert, J., Bruylants, A., Crooy, P. N-acyl- -aminonitriles in the Pinner reaction. Synthesis 9 2, 622-624. 

Brook rearrangement, reverse 44, 514 Bruylants-type reaction 44, 899 1,3-Butadienes... 

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