Claisen rearrangement of allylfluorovinyl ethers
TL;DR: In this paper, the synthesis of α-fluoro β-substituted γ-unsaturated acid derivatives via a diastereoselective Claisen rearrangement of allyldifluorovinyl ethers is described.
About: This article is published in Journal of Fluorine Chemistry.The article was published on 1998-07-09. It has received 15 citations till now. The article focuses on the topics: Carroll rearrangement & Sigmatropic reaction.
Citations
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TL;DR: The present review lists different methods for the preparation of fluorinated enol ethers, and sums up their numerous synthetic applications.
Abstract: Thanks to the beneficial effect of fluorine substitution on the pharmacokinetic properties of molecules, an ever increasing number of marketed drugs incorporate a fluorine atom into their structure. As a consequence, the synthesis of fluorinated molecules has become a very active research field. Among the numerous approaches, fluorinated enol ethers are valuable building blocks that allow the introduction of a fluoro- or difluoromethyl group through a wide variety of reactions. The present review lists different methods for their preparation and sums up their numerous synthetic applications.
84 citations
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TL;DR: In this paper, a review of functionalized fluoroalkyl and alicyclic silanes has been presented, focusing mainly on the chemistries of (1) 1-substituted difluoromethyl silanes (XCF2SiR3), (2) 2,2-diffluorovinylsilanes (CF2 CX SiR3) and (3) trifluorooisopropenyl, triffluoroacetimidoyl, and (4) other fluorinated alicycycl
43 citations
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TL;DR: For example, Ireland-Claisen rearrangement of 3-acetoxy-2-fluorodec-1-ene (9b) with triethylamine and TMSOTf in ether failed as discussed by the authors.
28 citations
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TL;DR: In this article, γ,γ-difluorinated allylic alcohols obtained from trifluoroethanol were esterified efficiently, in which chelation both controlled configuration and stabilised against fragmentation.
Abstract: Readily available γ,γ-difluorinated allylic alcohols obtained from trifluoroethanol were esterified efficiently. Exposure to strong base (LDA) afforded the ester enolates, in which chelation both controlled configuration and stabilised against fragmentation, which were trapped as their silyl ketene acetals. Rearrangement occurred to afford base-sensitive acid products. Esterification under mild conditions afforded the purifiable methyl esters in which the masked ketone had been released. Educts with either a benzyloxy or an allyloxy group at the α-position could be deprotected releasing the alcohols.
20 citations
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TL;DR: Sigmatropic rearrangement as mentioned in this paper transforms these intermediates into species in which the fluorine atom (or atoms) is borne on an sp3-hybridised carbon.
17 citations
References
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139 citations
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TL;DR: Etude de l'induction asymetrique trans-1,3 au cours de l',halogenolactonisation des dimethylamides des acides α-methyl- ou α-benzyl alcene-4oiques ou alcENE-4thioiques conduisant aux perhydrofurannones-2 and -thiophenones -2 trans-disubstituees-3,5 (les acidesα,β-dissubstitues conduisent aux (thio
Abstract: Etude de l'induction asymetrique trans-1,3 au cours de l'halogenolactonisation des dimethylamides des acides α-methyl- ou α-benzyl alcene-4oiques ou alcene-4thioiques conduisant aux perhydrofurannones-2 et -thiophenones-2 trans-disubstituees-3,5 (les acides α,β-disubstitues conduisent aux (thio) lactones trisubstituees-3,4,5)
110 citations