Oxazoline directed nucleophilic additions

Oxazoline-directed conjugate addition of nucleophiles to a naphthalene nucleus is one of the most useful methods to prepare dihydronaphthalenes. Since Meyers last comprehensive review, the focus has been directed to stereoselective synthesis of these important compounds. Meyers laboratory has continued their preeminence in this field and has expanded the scope and applications of this reaction. 

Coordination to strongly orf/zo-directing groups is responsible for the regiochemistry of some other reactions which do not involve ortholithiation. For example, while the electron-withdrawing nature of the oxazoline would be expected to direct the addition of the organolithium nucleophile to benzyne 11 towards the meta position, the major product that arises is the result of addition at the ortho position to give 12 (Scheme 1). ... 

The first step of this method involves a Knoevenagel-type condensation of TosMIC to provide intermediate 36a [28], It is noteworthy that the conditions used helped (a) cope with the lower activity of the 17-oxo group of 35 and (b) avoid elimination of sulfinic acid. The second step involves the condensation of 36a with formaldehyde (9c) to form intermediate 38, which then undergoes an internal nucleophilic attack onto the isocyanide carbon to generate the oxazoline intmnediate 39. Addition of 10 equivalents of MeOH to the phase transfer catalyst directly generates oxazoline 41 via the elimination of tosyl sulfonic acid from 40. Acid-catalyzed hydrolysis provides the target compound 37 (Scheme 7.8). 

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