Synthesis of cyclic alkenyl dimethylsiloxanes from alkynyl benzyldimethylsilanes and application in polyene synthesis
Cyclic dimethylalkenylsiloxanes, useful motifs for (Z)-selective Hiyama cross-coupling, are accessed from alkynyl benzyldimethylsilanes featuring adjacent allylic or homoallylic oxygen substituents by semihydrogenation/debenzylation/cyclization. While formation of 5- and 6-membered rings can be achi...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
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American Chemical Society
2019
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| _version_ | 1797110450099322880 |
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| author | Gudmundsson, HG Kuper, CJ Cornut, D Urbitsch, F Elbert, BL Anderson, EA |
| author_facet | Gudmundsson, HG Kuper, CJ Cornut, D Urbitsch, F Elbert, BL Anderson, EA |
| author_sort | Gudmundsson, HG |
| collection | OXFORD |
| description | Cyclic dimethylalkenylsiloxanes, useful motifs for (Z)-selective Hiyama cross-coupling, are accessed from alkynyl benzyldimethylsilanes featuring adjacent allylic or homoallylic oxygen substituents by semihydrogenation/debenzylation/cyclization. While formation of 5- and 6-membered rings can be achieved from the free alcohols using fluoride or silanolate, allylic acetate precursors to 5-membered rings display distinct modes of activation. The utility of these compounds is demonstrated through the preparation of a variety of (Z)-alkene-containing polyenes and application to a concise total synthesis of leukotriene B3. |
| first_indexed | 2024-03-07T07:55:02Z |
| format | Journal article |
| id | oxford-uuid:c40a8439-587d-4773-876b-c0f6a52b2d9d |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T07:55:02Z |
| publishDate | 2019 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:c40a8439-587d-4773-876b-c0f6a52b2d9d2023-08-11T10:32:00ZSynthesis of cyclic alkenyl dimethylsiloxanes from alkynyl benzyldimethylsilanes and application in polyene synthesisJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:c40a8439-587d-4773-876b-c0f6a52b2d9dEnglishSymplectic Elements at OxfordAmerican Chemical Society2019Gudmundsson, HGKuper, CJCornut, DUrbitsch, FElbert, BLAnderson, EACyclic dimethylalkenylsiloxanes, useful motifs for (Z)-selective Hiyama cross-coupling, are accessed from alkynyl benzyldimethylsilanes featuring adjacent allylic or homoallylic oxygen substituents by semihydrogenation/debenzylation/cyclization. While formation of 5- and 6-membered rings can be achieved from the free alcohols using fluoride or silanolate, allylic acetate precursors to 5-membered rings display distinct modes of activation. The utility of these compounds is demonstrated through the preparation of a variety of (Z)-alkene-containing polyenes and application to a concise total synthesis of leukotriene B3. |
| spellingShingle | Gudmundsson, HG Kuper, CJ Cornut, D Urbitsch, F Elbert, BL Anderson, EA Synthesis of cyclic alkenyl dimethylsiloxanes from alkynyl benzyldimethylsilanes and application in polyene synthesis |
| title | Synthesis of cyclic alkenyl dimethylsiloxanes from alkynyl benzyldimethylsilanes and application in polyene synthesis |
| title_full | Synthesis of cyclic alkenyl dimethylsiloxanes from alkynyl benzyldimethylsilanes and application in polyene synthesis |
| title_fullStr | Synthesis of cyclic alkenyl dimethylsiloxanes from alkynyl benzyldimethylsilanes and application in polyene synthesis |
| title_full_unstemmed | Synthesis of cyclic alkenyl dimethylsiloxanes from alkynyl benzyldimethylsilanes and application in polyene synthesis |
| title_short | Synthesis of cyclic alkenyl dimethylsiloxanes from alkynyl benzyldimethylsilanes and application in polyene synthesis |
| title_sort | synthesis of cyclic alkenyl dimethylsiloxanes from alkynyl benzyldimethylsilanes and application in polyene synthesis |
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