Pujari, Sandip A. ; Kaliappan, Krishna P. ; Valleix, Alain ; Grée, Danielle ; Grée, René (2008) A rapid access to new fluorinated 1,3-dienes and benzylic fluorides via metathesis on propargylic fluorides Synlett, 2008 (16). pp. 2503-2507. ISSN 0936-5214
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Official URL: https://www.thieme-connect.com/products/ejournals/...
Related URL: http://dx.doi.org/10.1055/s-2008-1078179
Abstract
The cross enyne metathesis reaction of propargylic fluoride (+)-12 with ethylene affords the enantioenriched 1,3-diene (+)-14 having fluorine-containing side chain at 2-position in good yield. Upon Diels-Alder reaction, followed by aromatization, this diene affords the new benzylic fluorides (+)-16 and (+)-17 in high ee values. This new strategy has been successfully extended to the corresponding gem-difluoro diene 21 and benzylic fluorides 23 and 24.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Thieme Medical Publishers Inc. |
| Keywords: | Dehydroxyfluorination; Enyne Metathesis; Diels-Alder Reaction; Aromatization; Benzylic Fluorides |
| ID Code: | 104972 |
| Deposited On: | 19 May 2017 10:29 |
| Last Modified: | 19 May 2017 10:29 |
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