Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines
Studies towards a N,N′-bis(p-methoxybenzyl)diketopiperazine asymmetric glycine cation equivalent for the synthesis of homochiral α-amino acids are described. The oxidation of enolate 3 with molecular oxygen provides either a mixture of hydroxylated diketopiperazines 7 and 8 or trione 10 depending up...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2002
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| _version_ | 1826264442330939392 |
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| author | Bull, S Davies, S Garner, A O'Shea, MD Savory, E Snow, E |
| author_facet | Bull, S Davies, S Garner, A O'Shea, MD Savory, E Snow, E |
| author_sort | Bull, S |
| collection | OXFORD |
| description | Studies towards a N,N′-bis(p-methoxybenzyl)diketopiperazine asymmetric glycine cation equivalent for the synthesis of homochiral α-amino acids are described. The oxidation of enolate 3 with molecular oxygen provides either a mixture of hydroxylated diketopiperazines 7 and 8 or trione 10 depending upon the reaction conditions. The nucleophilic reduction of trione 10 and the reaction of acetoxy N-acyliminium ion precursors 5 and 6, derived from 7 and 8, with allyltrimethylsilane and boron trifluoride etherate is examined and a model for the stereoselectivity observed in these additions is presented. |
| first_indexed | 2024-03-06T20:07:52Z |
| format | Journal article |
| id | oxford-uuid:29852d39-6a74-4f00-848d-51acc5782c98 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T20:07:52Z |
| publishDate | 2002 |
| record_format | dspace |
| spelling | oxford-uuid:29852d39-6a74-4f00-848d-51acc5782c982022-03-26T12:19:37ZChiral glycine cation equivalents: N-acyliminium species derived from diketopiperazinesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:29852d39-6a74-4f00-848d-51acc5782c98EnglishSymplectic Elements at Oxford2002Bull, SDavies, SGarner, AO'Shea, MDSavory, ESnow, EStudies towards a N,N′-bis(p-methoxybenzyl)diketopiperazine asymmetric glycine cation equivalent for the synthesis of homochiral α-amino acids are described. The oxidation of enolate 3 with molecular oxygen provides either a mixture of hydroxylated diketopiperazines 7 and 8 or trione 10 depending upon the reaction conditions. The nucleophilic reduction of trione 10 and the reaction of acetoxy N-acyliminium ion precursors 5 and 6, derived from 7 and 8, with allyltrimethylsilane and boron trifluoride etherate is examined and a model for the stereoselectivity observed in these additions is presented. |
| spellingShingle | Bull, S Davies, S Garner, A O'Shea, MD Savory, E Snow, E Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines |
| title | Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines |
| title_full | Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines |
| title_fullStr | Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines |
| title_full_unstemmed | Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines |
| title_short | Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines |
| title_sort | chiral glycine cation equivalents n acyliminium species derived from diketopiperazines |
| work_keys_str_mv | AT bulls chiralglycinecationequivalentsnacyliminiumspeciesderivedfromdiketopiperazines AT daviess chiralglycinecationequivalentsnacyliminiumspeciesderivedfromdiketopiperazines AT garnera chiralglycinecationequivalentsnacyliminiumspeciesderivedfromdiketopiperazines AT osheamd chiralglycinecationequivalentsnacyliminiumspeciesderivedfromdiketopiperazines AT savorye chiralglycinecationequivalentsnacyliminiumspeciesderivedfromdiketopiperazines AT snowe chiralglycinecationequivalentsnacyliminiumspeciesderivedfromdiketopiperazines |