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Aziridinyl alkynes strike gold: A novel gold(I)-catalyzed domino transformation of aziridinyl alkynes with arenes to construct 1,2,3,4-tetrahydroisoquinoline and 3,4-dihydroisoquinoline structural motifs (see scheme), especially sterically congested syn-3,4-disubstituted 1,2,3,4-tetrahydroisoquinolines, is described. A plausible mechanism proceeding through a benzylic cation is given based upon deuterium-labeling and control experiments as well as the observed diastereoselectivities.
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Zhang et al. (2010) studied this question.
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