2-Aminobenzyl chloride can undergo a 1,4 elimination reaction to form Aza-ortho-xylylenes. For example, compound (1-80) under the conditions of 22Cs2CO3/CH2Cl2 undergoes a 1,4 elimination to remove one molecule of HCl to form Aza-ortho-xylylenes. Then, under basic conditions, the configuration changes, and an intramolecular Diels-Alder reaction occurs, giving compound (1-81) in a very high yield with an ee value of 99%.
