Enantiorecognition phenomena in asymmetric synthesis
<p>This thesis is concerned with investigations into applications of double asymmetric induction and parallel kinetic resolution in asymmetric synthesis.</p><p>Chapter 1 introduces enantiorecognition phenomena as a significant field in asymmetric synthesis. The main approaches in t...
| Những tác giả chính: | , |
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| Định dạng: | Luận văn |
| Ngôn ngữ: | English |
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2011
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| Những chủ đề: |
| _version_ | 1826283539464716288 |
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| author | Yin, J Jingda yin |
| author2 | Davies, S |
| author_facet | Davies, S Yin, J Jingda yin |
| author_sort | Yin, J |
| collection | OXFORD |
| description | <p>This thesis is concerned with investigations into applications of double asymmetric induction and parallel kinetic resolution in asymmetric synthesis.</p><p>Chapter 1 introduces enantiorecognition phenomena as a significant field in asymmetric synthesis. The main approaches in this field are described: double asymmetric induction, kinetic resolution, parallel kinetic resolution and dynamic kinetic resolution.</p><p>Chapter 2 describes investigations into the use of double asymmetric induction as a mechanistic probe to elucidate the reactive conformation of enantiopure α,β-unsaturated esters (derived from Corey’s 8-phenylmenthol auxiliary) and hydroxamates [derived from (S)-N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine] upon conjugate addition.</p><p>Chapter 3 describes investigations into the doubly diastereoselective organocatalytic intramolecular Michael cyclization of enantiopure enamides (derived from a 4-substituted-5,5-dimethyl-oxazolidin-2-one auxiliary) and α,β-unsaturated esters (derived from Corey’s 8-phenylmenthol auxiliary) using α-methylbenzylamine and its derivatives as the chiral catalysts.</p><p>Chapter 4 describes investigations into parallel kinetic resolution of acyclic γ-amino-α,β-unsaturated esters utilising a 50:50 pseudoenantiomeric mixture of lithium amides. To highlight the synthetic utility of the resultant β,γ-diamino esters, their elaboration to a range of 5-substituted-4-amino-pyrrolidin-2-ones is demonstrated and a concise synthesis of natural product (±)-absouline is performed.</p><p>Chapter 5 contains full experimental procedures and characterisation data for all compounds synthesised in chapters 2, 3 and 4.</p> |
| first_indexed | 2024-03-07T01:00:23Z |
| format | Thesis |
| id | oxford-uuid:89838860-52f1-4cdb-94e9-112d5bf0ef4b |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T01:00:23Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | oxford-uuid:89838860-52f1-4cdb-94e9-112d5bf0ef4b2022-03-26T22:25:10ZEnantiorecognition phenomena in asymmetric synthesisThesishttp://purl.org/coar/resource_type/c_db06uuid:89838860-52f1-4cdb-94e9-112d5bf0ef4bChemistry & allied sciencesOrganic chemistryEnglishOxford University Research Archive - Valet2011Yin, JJingda yinDavies, S<p>This thesis is concerned with investigations into applications of double asymmetric induction and parallel kinetic resolution in asymmetric synthesis.</p><p>Chapter 1 introduces enantiorecognition phenomena as a significant field in asymmetric synthesis. The main approaches in this field are described: double asymmetric induction, kinetic resolution, parallel kinetic resolution and dynamic kinetic resolution.</p><p>Chapter 2 describes investigations into the use of double asymmetric induction as a mechanistic probe to elucidate the reactive conformation of enantiopure α,β-unsaturated esters (derived from Corey’s 8-phenylmenthol auxiliary) and hydroxamates [derived from (S)-N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine] upon conjugate addition.</p><p>Chapter 3 describes investigations into the doubly diastereoselective organocatalytic intramolecular Michael cyclization of enantiopure enamides (derived from a 4-substituted-5,5-dimethyl-oxazolidin-2-one auxiliary) and α,β-unsaturated esters (derived from Corey’s 8-phenylmenthol auxiliary) using α-methylbenzylamine and its derivatives as the chiral catalysts.</p><p>Chapter 4 describes investigations into parallel kinetic resolution of acyclic γ-amino-α,β-unsaturated esters utilising a 50:50 pseudoenantiomeric mixture of lithium amides. To highlight the synthetic utility of the resultant β,γ-diamino esters, their elaboration to a range of 5-substituted-4-amino-pyrrolidin-2-ones is demonstrated and a concise synthesis of natural product (±)-absouline is performed.</p><p>Chapter 5 contains full experimental procedures and characterisation data for all compounds synthesised in chapters 2, 3 and 4.</p> |
| spellingShingle | Chemistry & allied sciences Organic chemistry Yin, J Jingda yin Enantiorecognition phenomena in asymmetric synthesis |
| title | Enantiorecognition phenomena in asymmetric synthesis |
| title_full | Enantiorecognition phenomena in asymmetric synthesis |
| title_fullStr | Enantiorecognition phenomena in asymmetric synthesis |
| title_full_unstemmed | Enantiorecognition phenomena in asymmetric synthesis |
| title_short | Enantiorecognition phenomena in asymmetric synthesis |
| title_sort | enantiorecognition phenomena in asymmetric synthesis |
| topic | Chemistry & allied sciences Organic chemistry |
| work_keys_str_mv | AT yinj enantiorecognitionphenomenainasymmetricsynthesis AT jingdayin enantiorecognitionphenomenainasymmetricsynthesis |