| Sumari: | <p>This thesis demonstrates the ability of a rhodium(I)-phosphoramidite catalyst to effect the first
examples of kinetic resolution in [5+2] cycloisomerization (Scheme i). This methodology was
applied to a range of diversely substituted enyne substrates, including a novel chiral silane tether.
Depending on the substrate, either a classical resolution, or a diastereodivergent resolution was
achieved, both with exceptional selectivity.</p>
<p>Furthermore, this methodology was applied to the asymmetric synthesis of the natural product (+)-
dictamnol, a trinorguaiane sesquiterpene isolated from the roots of Dictamnus dascarpus TURCZ,
with diastereodivergent resolution of an allene vinylcyclopropane as the key step.</p>
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