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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| Other Authors: | |
| Format: | Thesis |
| Language: | English |
| Published: |
2020
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| Subjects: |
| _version_ | 1797110585172688896 |
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| author | Ma, K |
| author2 | Anderson, E |
| author_facet | Anderson, E Ma, K |
| author_sort | Ma, K |
| collection | OXFORD |
| description | <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> |
| first_indexed | 2024-03-07T07:56:52Z |
| format | Thesis |
| id | oxford-uuid:00b41d6a-2a81-4e90-a3b3-a4ca9b418d45 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T07:56:52Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | oxford-uuid:00b41d6a-2a81-4e90-a3b3-a4ca9b418d452023-09-04T07:41:32ZKinetic resolution in rhodium-catalyzed [5+2] cycloisomerizationThesishttp://purl.org/coar/resource_type/c_db06uuid:00b41d6a-2a81-4e90-a3b3-a4ca9b418d45ChemistryEnglishHyrax Deposit2020Ma, KAnderson, E<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> |
| spellingShingle | Chemistry Ma, K Kinetic resolution in rhodium-catalyzed [5+2] cycloisomerization |
| title | Kinetic resolution in rhodium-catalyzed [5+2] cycloisomerization |
| title_full | Kinetic resolution in rhodium-catalyzed [5+2] cycloisomerization |
| title_fullStr | Kinetic resolution in rhodium-catalyzed [5+2] cycloisomerization |
| title_full_unstemmed | Kinetic resolution in rhodium-catalyzed [5+2] cycloisomerization |
| title_short | Kinetic resolution in rhodium-catalyzed [5+2] cycloisomerization |
| title_sort | kinetic resolution in rhodium catalyzed 5 2 cycloisomerization |
| topic | Chemistry |
| work_keys_str_mv | AT mak kineticresolutioninrhodiumcatalyzed52cycloisomerization |