The high nucleophilicity of the lithium derivative of (1), X = COtBu, permits alkylation at C-1 using primary alkyl chlorides, secondary alkyl iodides or easily deprotonated ketones. The pivaloyl group in the product (2) can be reductively removed. 1,1-Disubstituted tetra-hydroisoquinolines such as (3) can be obtained in this way.
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Lohmann et al. (1981) studied this question.
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