Kinetic resolution in rhodium-catalyzed [5+2] cycloisomerization

<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....

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Chi tiết về thư mục
Tác giả chính: Ma, K
Tác giả khác: Anderson, E
Định dạng: Luận văn
Ngôn ngữ:English
Được phát hành: 2020
Những chủ đề:
Miêu tả
Tóm tắt:<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>