Wagner-Meerwein rearrangements Ritter reaction

The enantioselective biomimetic total synthesis of the alkaloid (+)-aristotelone was accomplished by C.H. Heathcock and co-workers." The synthetic sequence commenced with a Hg(N03)2-mediated Ritter reaction between (1S)-(-)-P-pinene and 3-indolylacetonitrile. Upon protonation, the pinene underwent a Wagner-Meerwein rearrangement to generate a tertiary carbocation which reacted with the cyano group. The initially formed imine product was reduced to the corresponding amine by sodium borohydride in methanol. 

S Cascade reactions implementing the Ritter reaction Recent examples of the Ritter reaction have combined this useful synthetic tool with other reactions and rearrangements to produce complex reaction sequences. For example, Bishop has reported the combination of the Ritter reaction with the Wagner-Meerwein rearrangement, which can result in complex and sometimes unpredictable reaction sequences.17 The use of the Ritter reaction to trap cationic intermediates in the CAN-mediated dimerization of alkoxystyrenes has recently allowed the synthesis of a-aminotetralin derivatives by Nair.18... 

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