Silatropic carbonyl ene cyclizations in the synthesis of pseudosugars and hydroxylated piperidines.
[reaction: see text] We describe two applications of silicon-tethered thermal allyl transfer reactions of alpha-silyloxyaldehydes; formally, these processes can be regarded as silatropic carbonyl ene reactions in which the silicon tether is transferred to the aldehyde oxygen concurrent with carbonyl...
| Main Authors: | , , |
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| Format: | Journal article |
| Language: | English |
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2005
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| _version_ | 1797065707653955584 |
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| author | Robertson, J Stafford, P Bell, S |
| author_facet | Robertson, J Stafford, P Bell, S |
| author_sort | Robertson, J |
| collection | OXFORD |
| description | [reaction: see text] We describe two applications of silicon-tethered thermal allyl transfer reactions of alpha-silyloxyaldehydes; formally, these processes can be regarded as silatropic carbonyl ene reactions in which the silicon tether is transferred to the aldehyde oxygen concurrent with carbonyl allylation. In the first application, isoserinal substrates, which bear side-chain nitrogen functionality, are elaborated to dihydroxypiperidines. In the second application, a product of cyclohexadienyl transfer is taken on to carbocylic analogues of, for example, mannose. In both series, the silatropic ene reactions are effected thermally, with no added Lewis acid, and are both stereospecific and highly stereoselective. |
| first_indexed | 2024-03-06T21:32:25Z |
| format | Journal article |
| id | oxford-uuid:451c7306-455f-4ead-a5d2-91d1c36f9bf0 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T21:32:25Z |
| publishDate | 2005 |
| record_format | dspace |
| spelling | oxford-uuid:451c7306-455f-4ead-a5d2-91d1c36f9bf02022-03-26T15:05:53ZSilatropic carbonyl ene cyclizations in the synthesis of pseudosugars and hydroxylated piperidines.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:451c7306-455f-4ead-a5d2-91d1c36f9bf0EnglishSymplectic Elements at Oxford2005Robertson, JStafford, PBell, S[reaction: see text] We describe two applications of silicon-tethered thermal allyl transfer reactions of alpha-silyloxyaldehydes; formally, these processes can be regarded as silatropic carbonyl ene reactions in which the silicon tether is transferred to the aldehyde oxygen concurrent with carbonyl allylation. In the first application, isoserinal substrates, which bear side-chain nitrogen functionality, are elaborated to dihydroxypiperidines. In the second application, a product of cyclohexadienyl transfer is taken on to carbocylic analogues of, for example, mannose. In both series, the silatropic ene reactions are effected thermally, with no added Lewis acid, and are both stereospecific and highly stereoselective. |
| spellingShingle | Robertson, J Stafford, P Bell, S Silatropic carbonyl ene cyclizations in the synthesis of pseudosugars and hydroxylated piperidines. |
| title | Silatropic carbonyl ene cyclizations in the synthesis of pseudosugars and hydroxylated piperidines. |
| title_full | Silatropic carbonyl ene cyclizations in the synthesis of pseudosugars and hydroxylated piperidines. |
| title_fullStr | Silatropic carbonyl ene cyclizations in the synthesis of pseudosugars and hydroxylated piperidines. |
| title_full_unstemmed | Silatropic carbonyl ene cyclizations in the synthesis of pseudosugars and hydroxylated piperidines. |
| title_short | Silatropic carbonyl ene cyclizations in the synthesis of pseudosugars and hydroxylated piperidines. |
| title_sort | silatropic carbonyl ene cyclizations in the synthesis of pseudosugars and hydroxylated piperidines |
| work_keys_str_mv | AT robertsonj silatropiccarbonylenecyclizationsinthesynthesisofpseudosugarsandhydroxylatedpiperidines AT staffordp silatropiccarbonylenecyclizationsinthesynthesisofpseudosugarsandhydroxylatedpiperidines AT bells silatropiccarbonylenecyclizationsinthesynthesisofpseudosugarsandhydroxylatedpiperidines |