ChemInform Abstract: Asymmetric and Nonasymmetric Addition of RLi and RMgX to 3-Methoxynaphthalen-2-yl Oxazolines and Imines. An Approach to Substituted 2-Tetralones.
Abstract
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ChemInform Abstract
It is shown that the 3-methoxynaphthalen-2-yl oxazolines (I) and (VI) do not undergo aromatic nucleophilic substitution of the 3-MeO group with organolithium reagents but afford dihydronaphthalenes like (IV) and (VII). The latter can easily be transformed into aldehydes of type (VIII). These aldehydes can also be prepared via addition of Grignard reagents to 3-methoxynaphthalen-2-yl imines. The aldehydes are useful precursors of substituted 2-tetralones. The analogue containing a 2-carbomethoxy group is a highly versatile intermediate from which 4-, 3,4-, and 3,4,4-substituted 2-tetralones are available.
