| A stereoselective synthesis of 1,6-diphenyl-1,3,5-hexatrienes utilising 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane as a two-carbon alkenyl building block. | |
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MedLine Citation:
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PMID: 16106297 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A number of 1,6-diphenyl-1,3,5-hexatrienes of varying alkene geometries were stereoselectively prepared from just two starting materials: iodobenzene and 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane via a series of Heck, Suzuki-Miyaura and stereocontrolled iododeboronation reactions. These results demonstrate how 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane can be used as a genuine two-carbon vinyl-dianion building block in stereocontrolled polyene synthesis. |
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Authors:
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Andrew P Lightfoot; Steven J R Twiddle; Andrew Whiting |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2005-07-20 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 3 ISSN: 1477-0520 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2005 Sep |
Date Detail:
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Created Date: 2005-08-17 Completed Date: 2006-01-06 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 3167-72 Citation Subset: IM |
Affiliation:
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GlaxoSmithKline Pharmaceuticals, New Frontiers Science Park, Third Avenue, Harlow, Essex CM19 5AW, UK. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alkenes
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chemical synthesis* Boron Compounds / chemistry* Dioxanes / chemistry* Iodobenzenes / chemistry Ligands Molecular Structure Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane; 0/Alkenes; 0/Boron Compounds; 0/Dioxanes; 0/Iodobenzenes; 0/Ligands; 591-50-4/iodobenzene |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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