Abstract
The mono and dilithiation of benzyl-[2-(tosylmethyl)-2-propenyl]amine ( 4) with n-butyllithium affords the corresponding allylic anions 5a and 5b, respectively. Monoanion 5a reacts regioselectively at the α-position of the sulfone group with deuterium oxide, alkyl halides, propanal, methyl crotonate and ethyl propiolate. Dianion 5b reacts with alkyl halides and ethyl propiolate also at the nitrogen atom to give in the case of dihalides, 6, 7, and 8 member nitrogen-containing heterocycles.
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