Stereocontrolled ring-opening of some enantiomerically enriched epoxy ketones and epoxy alcohols using trimethylaluminium: synthesis of (S )-2-arylpropanoic acids

Carde, Lydia; Davies, Huw M. L.; Roberts, Stanley M.

doi:10.1039/b000996m

Cited by 33 publications

(6 citation statements)

References 23 publications

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“…Diastereoselective reduction of the epoxy ketone 5 with zinc borohydride furnished the anti ‐epoxy alcohol 6 (d.r. 92:8) . Configurational inversion of the secondary alcohol under Mitsunobu conditions and subsequent hydrolysis yielded the syn ‐epoxy alcohol 7 (d.r.…”

Section: Resultsmentioning

confidence: 99%

Emulating Natural Product Conformation by Cooperative, Non‐Covalent Fluorine Interactions

Scheidt

Selter

Santschi

et al. 2016

Chemistry A European J

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Pervasive in Nature, the propane unit is an essential component of numerous bioactive molecules. These range from acyclic systems, such as the neurotransmitter γ-aminobutyric acid, through to the bicyclic nuclei of various chromanes and dihydrobenzofurans. In the latter case, cyclisation via cyclic ether formation ensures a highly pre-organised structure, whilst linear scaffolds display more dynamic conformational behaviour resulting from rotation about the two internal C(sp )-C(sp ) bonds. In this study, the replacement of -[CH ]- units by -[CHF]- centres is evaluated as a strategy to achieve acyclic conformational control by hindering these internal rotations. Reinforcing, non-covalent fluorine interactions are validated as powerful design features that result in programmable conformational behaviours: These are encoded by the relative configuration of each centre. By exploiting cooperative neighbouring stereoelectronic effects in a multi-vicinal fluoroalkane it is possible to emulate the overall conformation of the dihydrobenzofuran scaffold found in a variety of natural products with an acyclic mimic. This is described as a function of two bond vectors at the chain termini and validated by combined theoretical, crystallographic and spectroscopic analyses. In view of the favourable physicochemical properties associated with fluorine introduction, this approach to bioactive scaffold design may prove to be expansive.

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Section: Resultsmentioning

confidence: 99%

Emulating Natural Product Conformation by Cooperative, Non‐Covalent Fluorine Interactions

Scheidt

Selter

Santschi

et al. 2016

Chemistry A European J

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“…Only in the case of the methyl ketone 10 was a mixture of diastereomers obtained on reaction with phenylmagnesium bromide, the major product 14 being contaminated with a small amount of the diastereoisomer 4 (ratio 4 : 14, 1 : 6). 4 The stereochemistry of the compounds 5 3 and 13 (Fig. 1) was ascertained by X-ray crystallography.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and reactions of some optically active epoxides formally derived from tertiary allylic alcohols

Bickley

Gillmore

Roberts

et al. 2001

J. Chem. Soc., Perkin Trans. 1

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“…α-Hydroxy ketone 14 was isolated and the spectroscopic data were in accordance with those described in the literature. [10] Scheme 6. Determination of the syn relative stereochemistry in 5c.…”

Section: Entry Solventmentioning

confidence: 99%

Reduction of Alkynyl α‐Hydroxy Esters: Stereoselective α‐Ketol Rearrangement

Hameury¹,

Bellosta²,

Guillemont³

et al. 2010

Eur J Org Chem

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Stereocontrolled ring-opening of some enantiomerically enriched epoxy ketones and epoxy alcohols using trimethylaluminium: synthesis of (S )-2-arylpropanoic acids

Cited by 33 publications

References 23 publications

Emulating Natural Product Conformation by Cooperative, Non‐Covalent Fluorine Interactions

Emulating Natural Product Conformation by Cooperative, Non‐Covalent Fluorine Interactions

Synthesis and reactions of some optically active epoxides formally derived from tertiary allylic alcohols

Reduction of Alkynyl α‐Hydroxy Esters: Stereoselective α‐Ketol Rearrangement

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