Thiophene congeners of Tröger's base were prepared by the reactions of 3-aminothiophenes and formaldehyde. Treatment of the thiophene congeners with BuLi or LDA resulted in the regioselective formation of the dianion at the 2- and 7-positions, which reacted with a variety of electrophiles such as trimethylsilyl chloride, iodine, NBS, DMF, benzophenone, and benzaldehyde. This reaction opens up a facile and versatile entry for a Tröger's base skeleton with a variety of functional groups.
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Kobayashi et al. (2002) studied this question.
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