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“Black belt” SNi and SNi′: Deuterium labeling revealed an inherent preference of N- and C-metalated nitriles for SNi, rather than SNi′ displacement. The fundamental reactivity preferences are harnessed in a series of cyclizations to cis- and trans-decalins that install contiguous quaternary–tertiary and quaternary–quaternary stereocenters (see scheme).
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Luján‐Montelongo et al. (2013) studied this question.
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